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Bidentated peptide chiral chromatographic silanes containing diamine structures and chiral chromatographic filler

A chiral and silane technology, applied in the field of liquid chromatography separation materials, can solve the problem that the service life of the coated chromatographic column is not as long as that of the bonded chromatographic column, and achieves good chiral separation effect, simple synthesis method, and easy scale expansion. Effect

Inactive Publication Date: 2014-06-25
北京迪马欧泰科技发展中心
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Currently, the most common commercially available chiral chromatographic packing is cellulose-based chromatographic packing. This type of chromatographic column is mainly coated. Although their chiral separation effect is better, the service life of the coated chromatographic column is not as good as that of the bonded chromatographic column.

Method used

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  • Bidentated peptide chiral chromatographic silanes containing diamine structures and chiral chromatographic filler
  • Bidentated peptide chiral chromatographic silanes containing diamine structures and chiral chromatographic filler
  • Bidentated peptide chiral chromatographic silanes containing diamine structures and chiral chromatographic filler

Examples

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Effect test

Synthetic example 1

[0039]

[0040]

[0041] main ingreadient :(1 R ,2 R )-1,2-Diphenylethylenediamine (cas No. 35132-20-8) M = 212.3

[0042] Fmoc protected phenylalanine (cas number 174132-31-1) M = 387.4

[0043] 3-isocyanatopropyltrimethoxysilane (cas number 15396-00-6) d=1.084, M=205

[0044] Silica gel pretreatment

[0045] AGC Si-Tech spherical silica gel (pore size 100?, particle size 5 μm, specific surface area 450 m 2 / g, the metal impurity content is less than 30 ppm), according to the volume mass ratio of hydrochloric acid and silica gel 2 ml / g, mix 20% hydrochloric acid and silica gel by volume, heat to 100°C and reflux for 4h. Filter with suction, wash with deionized water until neutral, wash with methanol, and dry at 170°C for 24h.

[0046] Preparation of Silane 5

[0047] (1) Preparation of intermediate 3

[0048] 10.6g (50mmol) (1 R ,2 R )-1,2-Diphenylethylenediamine ( 1 ) dissolved in 400ml of dichloromethane, in N 2 Stir under protection. Take another ...

Synthetic example 2

[0062]

[0063]

[0064] Preparation of Silane 9

[0065] (1) Preparation of Intermediate 3

[0066] 10.6g (50mmol) (1 R ,2 R )-1,2-Diphenylethylenediamine ( 1) Dissolve in 500ml dichloromethane, in N 2 Stir under protection. Take another clean beaker, weigh 42.6g (110mmol) Fmoc-Phe-OH ( 2） , 110mmol HBTU, 110mmol HOBT, add 50ml DMF / 50ml dichloromethane and 100ml DIEA. Stir to activate and protect the amino acid for 5-10 minutes, and add the transparent solution after activation ( 1 ) reaction system, stirred at room temperature for 2-3h. The reaction was detected by TLC spot plate until the reactant ( 1 )disappear. The reaction mixture was rotary evaporated to remove dichloromethane, the concentrate was added to refrigerated diethyl ether for precipitation, washed with cold diethyl ether three times to remove the remaining impurities and solvent, and purified by flash column chromatography to obtain the intermediate ( 3 ). MS: m / z 952.12 [M+H] + . Eleme...

Synthetic example 3

[0084]

[0085] Preparation of cyclohexanediamine-monopolyphenylalanine silane

[0086] ① Preparation of Intermediate 13: Weigh raw materials ( 12 ) 12.4g (32mmol), added to the three-necked bottle. Install a condenser tube and a dropping funnel, and feed dry nitrogen. Add dry toluene 80ml, trifluoroacetic anhydride (TFAA) 8.0g, stir at room temperature until ( 12 )completely dissolved. Add ingredients ( 11 ) 1.7g (15mmol), stirred for 24h. Add 100ml of ethyl acetate to dilute, separate the layers, wash the ethyl acetate layer with 2N sodium hydroxide solution, concentrated hydrochloric acid and water twice, and combine the organic phases. Dry over anhydrous sodium sulfate, filter, and remove the solvent under reduced pressure to give the crude product. Purified by flash column chromatography to obtain a white solid intermediate ( 13 ) 8.3g, yield 90.5%.

[0087] MS: m / z 608.36[M] + , 495.56[M-tBu+H] + . Elemental analysis: C%67.02, H%7.78, N%8.97.

[0088] ...

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Abstract

The invention discloses bidentated peptide chiral chromatographic silanes containing diamine structures and a chiral chromatographic filler. The invention discloses bidentated chiral silanes as shown in structural formula (I), wherein R1, R2 and R3 are alkyl, naphthenic base, aryl and heterocyclic radical; n is an integer from 1 to 10; alpha is 0, 1, and 2; X is halogen, alkoxy, acyloxy or amino. The bidentated peptide chiral chromatographic silanes containing diamine structures are simple and convenient in synthetic method, good in chiral separating effect and easy for scale expansion.

Description

technical field [0001] The invention relates to a class of bidentate peptide chiral chromatographic silanes and cyclic chiral chromatographic fillers synthesized from diamines, and belongs to the technical field of liquid chromatographic separation materials. Background technique [0002] There are often significant differences in the activity, toxicity, and metabolic pathways of chiral drug L-isomers and D-isomers in organisms. Many drugs, pesticides, insect pheromones, etc. are chiral compounds, and 1045 of the more than 1850 drugs commonly used in clinical practice are chiral drugs. With the rapid development of proteomics, metabolomics, modernization of traditional Chinese medicine and other research fields, a large number of chemically synthesized and naturally isolated chiral compounds have emerged. They often have multiple chiral centers and multiple optical isomers, and The physiological activities and medicinal effects of various isomers are not the same. The sepa...

Claims

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Application Information

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IPC IPC(8): C07K5/062C07F7/18B01J20/29B01J20/30
Inventor 李广庆孙晓莉
Owner 北京迪马欧泰科技发展中心
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