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Convenia synthetic method and Convenia sodium salt synthetic method

A synthesis method and technology of cefvecin, applied in the field of pharmaceutical compounds, can solve problems such as unfavorable operation, cost saving, harsh reaction conditions, and difficult operation, and achieve the effects of low equipment requirements, mild reaction conditions, and improved process

Active Publication Date: 2016-01-20
GUANGDONG WENS DAHUANONG BIOTECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, this method has a long route, low yield, harsh reaction conditions, high environmental protection requirements, and difficult operation, so it is not conducive to operation and cost saving when used in mass production.

Method used

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  • Convenia synthetic method and Convenia sodium salt synthetic method

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preparation example Construction

[0032] A kind of synthetic method of cefotaxime of the present invention comprises the following steps:

[0033] (1) Bromination: dissolve ceftizoxime sodium (GHYA) intermediate formula (I) in an organic solvent, then cool down to 3°C, slowly add brominating agent dropwise, then add alkali, and react at 0-5°C for 2 Hours, after the reaction is complete, adjust the pH to 2, add water, extract, the water phase is sequentially extracted with petroleum ether and an organic solvent, adjust the pH of the water phase to 9, and after the organic solvent extraction, concentrate and dry to obtain the brominated product formula (II);

[0034]

[0035] (2) Electrophilic addition: Dissolve dihydrofuran in toluene, add benzenesulfinic acid and HBF at room temperature 4 organic solvent, stirred for reaction, extracted with ethyl acetate, concentrated, dried, and HPLC chiral separation to obtain white solid product benzenesulfinic acid-2S-tetrahydrofuryl ester;

[0036] (3) Nucleophilic s...

Embodiment 1

[0055] (6R,7R)-3-Bromo-8-oxo-7-[(phenylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2- Synthesis of Diphenylmethyl Carboxylate:

[0056] In the low-temperature reaction tank, add 20gGHYA and 320ml dichloromethane into a 500ml three-necked flask, then cool to 3°C, stir, and slowly add 10.8ml of phosphorus tribromide in dichloromethane solution dropwise for 10 minutes, then slowly Slowly add 5.2ml of triethylamine dropwise, the pH of the reaction solution is slightly alkaline, stir at 3°C ​​for 2 hours, and monitor the end point of the reaction by thin-layer chromatography. After the reaction is complete, add 150ml of distilled water, adjust the pH to 2 with 3N HCL, separate the liquids, extract the organic phase with an acidic water phase, combine the water phases, and extract the water phase with petroleum ether and dichloromethane twice, keep the water phase, and then Add 150ml of dichloromethane, adjust the pH to 9 with 5N NaOH, separate the layers, extract the aqueous...

Embodiment 2

[0059] Synthesis of benzenesulfinic acid-2S-furyl ester:

[0060] Add 5g of benzenesulfinic acid, 2.8g of dihydrofuran, and 60ml of toluene into a 250ml three-necked flask, cool down to 10°C, and add 60ml containing 0.5g of HBF 4 dichloromethane solution, stirred and reacted at 25°C for 2 hours, and the end point of the reaction was monitored by thin-layer chromatography. After the reaction was completed, 50ml of water was added, and the aqueous phase was separated. The organic phase was extracted twice with the aqueous phase, and the organic phase was dried over anhydrous sodium sulfate. Concentrated under reduced pressure, dried in vacuo, and chiral separation by HPLC (n-hexane:isopropanol) gave 3.34g of benzenesulfinic acid-2R-furyl ester, yield 44.7%, melting point 61-63°C, MS-ESI (M+1) :213.26; NMR results are as follows:

[0061] 1 HNMR (DMSO) δ: 7.52 (d, 2H), 7.41 (d, 2H), 4.67 (s, 2H);

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Abstract

The invention discloses a Convenia synthetic method and a Convenia sodium salt synthetic method. A ceftizoxime sodium midbody is taken as the raw material and is subjected to bromination, electrophilic addition, nucleophilic substitution, deprotection, amidation and the like to obtain Convenia and Convenia sodium salt. According to the Convenia synthetic method, synthetic routes and steps are simplified through technology improvement and reaction condition improvement, and cost is saved. The Convenia synthetic method and the Convenia sodium salt synthetic method are easy to operate, mild in reaction condition, low in requirement for production equipment, and capable of creating sound conditions for industrialization. It shows through analysis and detection that a prepared product is high in quality and can meet the requirements of industrial and agricultural production.

Description

technical field [0001] The invention relates to the field of pharmaceutical compounds, in particular to a synthesis method of cefotaxime and its sodium salt. Background technique [0002] Cephalosporins are semi-synthetic antibiotics containing cephems in their molecules. Belonging to β-lactam antibiotics, it is a derivative of 7-aminocephalosporanic acid (7-ACA) in β-lactam antibiotics, so they have similar bactericidal mechanisms. This class of drugs can destroy the cell wall of bacteria and kill bacteria during the reproduction period. It has a strong selective effect on bacteria, but has almost no toxicity to humans. It has the advantages of broad antibacterial spectrum, strong antibacterial effect, resistance to penicillinase, and less allergic reactions than penicillins. It is an important antibiotic with high efficiency, low toxicity and wide clinical application. . Cefovecin (Cefovecin) is a third-generation cephalosporin drug, its molecular structure is: [0003...

Claims

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Application Information

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IPC IPC(8): C07D501/20C07D501/06C07D501/12
CPCC07D501/06C07D501/12C07D501/20
Inventor 陈良柱方炳虎潘志坤刘雅红陈明贺利民
Owner GUANGDONG WENS DAHUANONG BIOTECH
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