106 results about "Ylide" patented technology

A process for the preparation of alkyl esters of N-protected oxo-azacycloalkylcarboxylic acids of Formula III: comprises contacting a ketosulfoxonium ylide of Formula II: with an iridium catalyst to obtain Compound III, wherein PG1 is an amine protective group; k is 0, 1, or 2; and RU, R1, R2, and R3 are defined herein. An embodiment of the process further com rises contacting a compound of Formula I: with a sulfoxonium halide of formula (RU)3S(O)Z, wherein Z is halide, in the presence of a strong base to obtain Compound II. Additional embodiments add a series of process steps leading to the synthesis of 7-oxo-1,6-diazabicyclo[3.2.1]octanes suitable for use as β-lactamase inhibitors.

The invention relates to the medicine chemical synthesis field, and especially discloses a preparation method of a Ticagrelor intermediate. The preparation method comprises the following steps: 1) taking 3,4-difluorobenzaldehyde (I) as an initial raw material, reacting with a phosphorus ylide material liquid to obtain (E)-3-(3,4-difluorophenyl)-2-acrylic acid ester (II); 2) performing a Simons-Smith asymmetric cyproteronethe reaction on the (E)-3-(3,4-difluorophenyl)-2-acrylic acid ester (II) to obtain trans-(1R,2R)-2-(3,4-difluorophenyl) cyclopropanecarboxylic acid ester (III); 3) performing aminolysis on the trans-(1R,2R)-2-(3,4-difluorophenyl) cyclopropanecarboxylic acid ester to obtain trans-(1R,2R)-2-(3,4-difluorophenyl)cyclopropanecarboxamide (IV); and 4) performing a Huffman rearrangement reaction on the trans-(1R,2R)-2-(3,4-difluorophenyl)cyclopropanecarboxamide (IV) to obatain the Ticagrelor intermediate (V). The method of the invention has the advantages of simple process, convenient operation, mild reaction condition and easy control, low cost and easy acquisition of raw material, high product yield and product purity, and is adapted to large scale industrial production.

The present invention discloses cinnamide compound synthesizing process. Inside water phase and in the presence of triphenyl phosphine, inorganic alkali and inorganic salt, bromoacetylamide and aromatic aldehyde react to synthesize cinnamide compound. During the convergent synthesis process, bromoacetylamide and triphenyl phosphine first react to produce quarternary ammonium salt as intermediate, the quarternary ammonium salt then reacts with alkali to produce corresponding ylide, and the ylide finally reacts with aromatic aldehyde to produce the cinnamide compound. The intermediate needs no separation, and this results in less reaction steps, short reaction period, low power consumption, high yield and reduced effluent. In addition, the present invention performs reaction in water phase to avoid use harmful expensive organic solvent.

A method for making epothilones and epothilone analogs is described, as are novel compounds made by the method. One embodiment of the method was used to synthesize epothilone B by a convergent approach that entailed Wittig coupling of an ylide derived from phosphonium bromide with an aldehyde. The former was prepared from propargyl alcohol by a nine-step pathway which installed both trisubstituted double bonds with clean Z configuration. Macrolactonization of a resulting seco acid provided the following intermediate diene epothilone analog. Selective saturation of the 9,10-olefin and subsequent epoxidation provided epothilone B.

Viscosifying polymers are effectively degraded during a well treatment operation with an ylide breaker or a vitamin B cofactor. The vitamin B cofactor is an ylide, vitamin B1, vitamin B2, vitamin B3, vitamin B6, vitamin B9 or vitamin B12 or mixtures thereof. Such breakers are effective at room and elevated temperatures and high pH environments.

A process for the epoxidation of 17-oxo-15,16-methylene steroids, in particular of drospirenone precursors, comprising the use of sulfoxonium ylides, in particular of dimethylsulfoxonium methyl ylide. The process allows to prepare in good yields 17-spiro epoxides, which can be easily transformed into 17-spironolacto-steroids.

The invention discloses a preparation method of (E)-3-[4-(4-fluorophenyl)-6-isopropyl-2-(N-methyl-N-methanesulfonylamino) pyrimidine-5-yl] acrolein which can be used as a rosuvastatin intermediate. The preparation method comprises the following steps: reacting 4-(4-fluorophenyl)-6-isopropyl-2-(N-methyl-N-methanesulfonylamino) pyrimidine-5-yl-formaldehyde with a sulfur ylide reagent under an alkaline condition to generate an epoxide shown in the formula III; then, reducing in the presence of a metal catalyst to generate a compound shown in the formula II; and finally reacting the compound shown in the formula II to generate the target product. The preparation method is simple in process and low in cost; no expensive catalyst is used; the generation of byproducts is reduced effectively so that the post-treatment becomes simple and easy to operate; in addition, the reaction yield is improved greatly; and therefore, the preparation method is quite suitable for large-scale industrial production.

The invention discloses ionic liquids with a surface active function and a preparation method for the ionic liquids, and belongs to the technical field of chemical industry. The preparation method comprises the following steps of: reacting pyrrolidine, piperidine or hexamethyleneimine with sultone respectively to introduce a sulfonic acid group to obtain imine nitrogen heterocyclic ring ylids, washing by using ethyl acetate, drying, dissolving the ylids into water, adding an aqueous solution of dodecylbenzene sulfonic acid, heating in a water bath, distilling and dewatering a product, and purifying to obtain the ionic liquids with the surface active function. The ionic liquids contain a surface active group, namely a dodecylbenzene sulfonic acid radical, and five-membered to seven-membered ring imine groups, so the surface tension of the liquids can be reduced, the liquids have a good effect of promoting the generation of gas hydrates, the induction time of the hydrates can be shortened, the formation pressure of hydrates such as methane and carbon dioxide is reduced, and the formation temperature of the hydrates is raised.

Produced or flowback water from an underground reservoir having been treated with a fluid containing a viscosifying polymer and a vitamin B1 and / or ylide breaker may be recycled by deactivating the vitamin B1 and / or ylide breaker with a sulfur or phosphorus containing nucleophilic agent.

The invention relates to a phosphonium salt compound containing precursor of biphosphorus ylide cyclopentadienyl cyclocarbene as well as a preparation method and application thereof, which belong to the field of organic synthesis. The adopted technical scheme is as follows: the general formula of the phosphonium salt compound containing precursor of biphosphorus ylide cyclopentadienyl cyclocarbene: FORMULA, wherein R is alkyl or aryl, X is selected from F-, Cl-, Br-, I-, PF6-, BF4-, SbF6-, ClO4- or N3-. The preparation method of the phosphonium salt compound comprises the following steps of: adding 1, 1'-ferrocene bimercury compound, tertiary phosphine PR3 and palladium chloride to an organic solvent, refluxing under protection of N2, filtering, evaporating to dryness and recrystallizing to obtain the phosphonium salt compound. In addition, in the invention, the phosphonium salt compound is used as a catalyst ligand so that the phosphonium salt compound and the metal salt act togetherto catalyze and synthesize alpha-aryl derivatives of carbonyl compound by one step. The application test indicates that compared with traditional N-heterocyclocarbene ligand, the phosphonium salt compound has excellent catalytic activity.

The invention provides an acidic ionic liquid-coated polymeric core solid acid material catalyst and a preparation method thereof. The catalyst adopts imidazole containing ethylenic bonds, pyridine or a tertiary amine compound to react with propane sultone or butane sultone to obtain a ylide containing the ethylenic bonds, acidification is performed to obtain an ionic liquid monomer, divinylbenzene is self-polymerized in acetonitrile to form a polymeric core containing surface double bonds, and the prepared ionic liquid monomer and the polydivinylbenzene core are co-polymerized to form the acidic ionic liquid-coated polymeric core solid acid material catalyst. The catalyst material has the advantages of high thermal stability, easiness in contact with an active center, high acid value of above 3.0mmol / g, relatively large surface area and good catalytic effect, and can be used repeatedly.

The invention provides a preparation method of gefarnate. The preparation method is characterized by comprising the following steps: conducting phosphorylation reaction on bromobutyric acid ethyl ester and triphenylphosphine to obtain phosphorus ylide solution, conducting whittig reaction to the phosphorus ylide solution and geranylacetone to obtain farnesyl ethyl acetate; adding the farnesyl ethyl acetate into sodium hydroxide and N,N-dimethylformamide so as to conduct acidification reaction to obtain farnesyl acetic acid; and adding geraniol, dimethylbenzene and a polymerization inhibitor into farnesyl acetic acid for conducting heating reflux and vacuum concentration, and collecting fraction at 186-200 DEG C to obtain gefarnate. According to the method, the technical problems that the gefarnate obtained in the prior art is long in synthetic route, low in yield, low in yield purity, complicated in after-treatment, and not applicable to industrial production can be solved.

The invention relates to an emulsion polymerizing preparation method of polyethylene / silicon dioxide core-shell structure composite material in the technical field of composite materials. The method is that: bis-(1, 5-cyclooctadiene) nickel and ethyl 4,4,4-trifluoro-2-(triphenylphosphine ylide)-acetoacetic ester is dissolved in toluol or benzene, and then is stirred, thus obtaining ethylene polymerization catalyst. A supported catalyst is obtained by mixing the ethylene polymerization catalyst and middle-hole silicon dioxide nano granules functionalized by ethylene; by dispersing the supported catalyst in water, adding a surface active agent and carrying out an ultrasonic treatment, stable emulsion is obtained; at last, polyethylene / silicon dioxide emulsion is obtained by inputting the ethylene, increasing the temperature and polymerizing. After drying the emulsion, the annealing is carried out above the fusion temperature of the polyethylene, thus obtaining the polyethylene / silicon dioxide core-shell structure composite material. The composite material not only can be independently used as material, but also can be used as additives of other polymer nano-composite materials.

The invention discloses a method for synthetizing 2,3-disubstituted dihydrobenzofuran. Kinds of substituted 2,3-disubstituted dihydrobenzofurans can be obtained from simple ylide and substituted phenol by reactions under an alkali catalytic condition. The method disclosed by the invention is simple and practical in operation, available in raw materials, high in yield, and good in diastereoselectivity.

The invention provides a method for synthesizing Seocalcitol, which mainly solves the technical problem of high production cost, difficult product purification and the like in the conventional synthetic method. The method comprises the following steps of: performing a Wittig / Wittig-Horner Julia / Horner-Wadsworth-Emmons name reaction by utilizing an aldehyde intermediate 7 and a Ylide intermediate 2 under the action of an alkali to construct carbon-carbon double bonds so as to form a precursor compound 10 of Seocalcitol, and then performing an illumination reaction and a deprotection reaction to prepare Seocalcitol 11. The invention also provides a method for synthesizing the key Ylide intermediate 2. The method has the advantages of simple operation, no side reaction, convenient purification, high yield and low cost, and is suitable for preparing high-purity Seocalcitol products through industrial production.

A synthesis method of sulfo-group-containing sulfur ylide comprises the following steps: reacting synthesized sulfonate represented by formula (IV) with a methylation reagent at 220-260 DEG C for 1-6h to obtain sulfur ylide represented by formula (III) when the reaction is finished; and carrying out an epoxidation reaction on the sulfur ylide of formula (III) and carbonyl compounds represented byformula (II) in a solvent at a reaction temperature of 40-60 DEG C for 1-7 h under the action of an alkaline substance, carrying out post-treatment on the reacted solution to obtain an oxirane derivative represented by formula (I), and simultaneously treating and recovering the generated protosolid sulfonate. The invention also discloses an application of the sulfo-group-containing sulfur ylide.The product is small in irritation and easy to be dissolved in water; and when the product is applied to the epoxidation reaction, the raw material alkyl sulfonate can be recycled, so that the industrial cost is reduced, and the production efficiency is improved.

The invention provides a preparation method for vitamin A acetate. The preparation method comprises the following steps: carrying out an addition reaction on a C15 phosphonium salt and a C5 aldehyde in the presence of an alkali compound to generate an ylide salt; and subjecting the ylide to a decomposition reaction to obtain the vitamin A acetate, wherein the content of ylide in a reaction system in a reaction process is less than or equal to 0.06 mol / L. According to the preparation method, on the basis of a C15 + C5 Wittig reaction, the content of ylide in the reaction system in the reaction process is controlled, and the vitamin A acetate with high purity, high trans-isomerization selectivity and high yield is obtained. The preparation method is suitable for any-scale reaction and can be carried out in batches and conducted semi-continuously or completely continuously; and the obtained vitamin A acetate is low in chromatic value, good in oxidation resistance and thermal stability, low in deterioration rate, beneficial to long-term stable storage and very good in market competitiveness.

The invention belongs to the technical field of medicine synthesis, and especially discloses a method for preparing 7-amino-3-vinyl cephalosporanic acid. The preparation method takes GCLE as an initial raw material, the GCLE and sodium iodide and triphenylphosphine are reacted in a mixing system of an organic solvent and water to generate phosphine salt, a certain amount of alkali lye is added in an organic phase for reacting to generate the corresponding phosphorus ylide, excess free alkali in an organic phase is removed through washing, formaldehyde and ylide are added for a wittig reaction, the organic phase is concentrated to a certain weight, phenol is added for removing carboxyl protection, amino protection is removed, crystallization is carried out to obtain 7-AVCA. The synthesis method does not require a mixing organic solvent, can realize recovery of sodium iodide and formaldehyde, has the advantages of high product yield, good quality, no three wastes generation, and environmental protection, and is suitable for large scale industrial production.

The invention relates to iodine(III)-mediated radiofluorination. According to the invention, a process for fluorination of aromatic compounds employing iodonium ylides and applicable to radiofluorination using 18F is described. Processes, intermediates, reagents and radiolabelled compounds are described.

The present invention provides a method of preparing a phosphonium salt of the formula [R1R2R3P—CR4R5R6]X, comprising ball-milling a phosphine of the formula R1R2R3P with a compound of the formula XCR4R5R6; a method of preparing a phosphorus ylide of the formula R1R2R3P═CR4R5, comprising ball-milling a phosphonium salt of the formula [R1R2R3P—HCR4R5]X in the presence of a base; and a method of preparing an olefin of the formula R4R5C═CR7H or R4R5C═CR7R8, comprising ball-milling a phosphorus ylide of the formula R1R2R3P═CR4R5 with a compound of the formula R7C(O)H or R7C(O)R8. The inventive method produces phosphonium salts and phosphorus ylides by mechanical processing solid reagents under solvent-free conditions. The advantages of the present invention over conventional solution methods, include: (1) extremely high selectivity; (2) high yields; (3) low processing temperatures; (4) simple and scalable reactions using commercially available equipment; and (5) the complete elimination of solvents from the reaction.

The invention relates to a synthetic method of 4-[1-(2,3-dimethylphenyl)vinyl-1-R1-2-R2 imidazole, and mainly solves the technical problems of expensive reagents, complex operations, and no benefit to industrial production for existing synthetic methods. The technical scheme of the invention is that: the synthetic method of 4-[1-(2,3-dimethylphenyl)vinyl-1-R1-2-R2 imidazole allows phosphorus ylide and 2,3-dimethylphenyl-1-R1-2-R2 imidazole-4-ketone to react so as to synthesize 4-[1-(2,3-dimethylphenyl)vinyl-1-R1-2-R2 imidazole. The reaction needs stirring overnight (12-16 hours), and the reaction product is filtered, concentrated, washed and purified by a silica gel column. The product is an important intermediate in pharmaceutical synthesis.

The invention discloses a novel synthesis method of a ticagrelor intermediate (1R,2R)-2-(3,4-difluorophenyl) cyclopropane nitrile. The novel synthesis method comprises the following steps: firstly, carrying out amination reaction on a glucose molecule chiral auxiliary reagent and (2E)-3-(3,4-diflurophenyl) acryloyl chloride; secondly, carrying out cyclopropanation reaction on a reactant and a sulfur ylide reagent to obtain a N-glucosyl (1R,2R)-2-(3,4-diflurophenyl) cyclopropanecarboxamide; thirdly, carrying out beta-N-glycosylation reaction on the N-glucosyl(1R,2R)-2-(3,4-diflurophenyl) cyclopropanecarboxamide under the action of PPh3, CBr4, AgOTf and NH3 water. The novel method has the characteristics of shorter process route, low-priced and easily-obtained starting materials, high yield, good stereoselectivity, good enantioselectivity and the like; the production cost is reduced to a great extent and better benefits in economy are obtained.

Produced or flowback water from an underground reservoir having been treated with a fluid containing a viscosifying polymer and a vitamin B1 and / or ylide breaker may be recycled by deactivating the vitamin B1 and / or ylide breaker with a sulfur or phosphorus containing nucleophilic agent.

The invention discloses a synthesis method of alpha-quaternary carbon-alpha-hydroxy-beta-aminoketone. An alcohol, a diazo compound and 1,3,5-triaryl-1,3,5-triazine which are used as raw materials undergo a one-step three-component reaction in an organic solvent with Rh2(esp)2 as a catalyst, chiral phosphoric acid (CPA) as a cocatalyst and a molecular sieve as an additive to obtain the product at ahigh stereoselectivity and a high yield. The method has the advantages of good atom economy, good stereoselectivity, mild reaction conditions, high yield, and simplicity and safety in operation. Themethod realizes asymmetric Mannich reaction of hydroxyl ylides, and allows a series of optically pure alpha-quaternary carbon-alpha-hydroxy-beta-aminoketone derivatives to be synthesized.

The invention discloses a self-replacement reaction method for cis-methyl oleate by using a ruthenium Schiff base indenyl ylide catalyst. The self-replacement reaction method comprises the following steps: adding a catalyst C50H52ClN3ORu and cis-methyl oleate to a two-opening flask, stirring, and setting the reaction temperature to be 80 DEG C; performing repeated and alternate operations of vacuum pumping and nitrogen charging on a reaction container, finally adding methylbenzene under the condition of nitrogen protection, and then charging nitrogen for performing a closed reaction; preparing a gas chromatograph sample; selecting 1h, 2h, 3h, 4h, 5h and 6h as time points of gas chromatograph tests, and measuring the catalysis yield of methyl oleate self-catalytic reaction. The method has the characteristics of short preparation period, simple operation, high efficiency and energy saving, the methyl oleate self-replacement reaction can be completed within 24h, the yield is 48.3%, and the method has significant practical value.

The invention provides a preparation method for synthesizing intermediate compound of rosuvastatin calcium, which relates to a technique for synthesizing intermediate compound of Rosuvastatin Calcium. The intermediate compound is (R)-7-[4-(4-fluorophenyl)-6-isopropyl-2-(N-methyl-N-methylsulfonylamino) pyrimidin-5-yl]-3-(tert-butyl dimethyl silicon)oxy-5-carbonyl-6(E)-methyl heptene. The method uses N-[4-(4-fluorophenyl)-5-formoxyl-6-isopropyl pyridine-2-yl]-N-methyl sulfonamide and (3R)-3-(tertiary butyl dimethyl silicon)oxy-5-carbonyl-6-triphenylphosphine ylide methyl caproate as raw material, through Wittig reaction, crude product is produced, and then, the crude product is separated and purified by phase disengagement, adsorption and other postprocessing methods, furthermore, the intermediate compound is (R)-7-[4-(4-fluorophenyl)-6-isopropyl-2-(N-methyl-N-methylsulfonylamino) pyrimidin-5-yl]-3-(tert-butyl dimethyl silicon)oxy-5-carbonyl-6(E)-methyl heptene for synthesizing Rosuvastatin Calcium is obtained. The invention has the advantages of low cost, simple operation and good economic benefit, which is suitable for industrial production. The intermediate compound obtained by method provided by the invention can be used for preparing Rosuvastatin Calcium.

Vinylphenylpropionic acid derivatives; processes for producing the derivatives; polymers of the same; and radiosensitive resin compositions containing the polymers. The above polymers exhibit low radiation absorption and are useful as the resin component of radiosensitive resin compositions particularly suitable for chemically amplified resists. For example, t-butyl 4-vinylphenylpropionate is produced by (1) reacting t-butyl bromoacetate with tri(n-butyl)phosphine to obtain a quaternary phosphonium salt, (2) reacting this salt with a base to obtain a phosphorus ylide, (3) reacting this ylide with 2,4,6-tris(3',5'-di-t-butyl-4'-hydroxybenzyl)methyl-styrene to obtain a quaternary phosphonium salt, and (4) hydrolyzing this salt.

The invention belongs to the technical field of chemical synthesis, and particularly relates to a method for preparing polysubstituted thiophene, which is simple to operate, green, environment-friendly, high in yield and suitable for large-scale preparation. According to the method, sulfur-containing ylide and electron-deficient alkyne are used as initial raw materials, and tetra-substituted and tri-substituted thiophene, especially fluorinated thiophene, are prepared in dichloroethane without other catalysts or metal reagents under the condition of heating.

The invention relates to development of a novel positron drug [<18>F] TPO1 targeting translocation protein TSPO. According to the invention, a novel TSPO ligand TPO1 is designed and developed, labeling is realized by using <18>F and a spiro hypervalent iodine ylide precursor Pre1, and the novel TSPO targeted positron drug [<18>F] TPO1 is synthesized; in-vitro radiation self-development is carried out on a human brain slice subjected to gene sequencing, and a result shows that the medicine is relatively high in specificity and relatively weak in sensitivity to rs6971; and a PET dynamic scanning result of a rat living body shows that the probe can pass through a blood brain barrier.