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A kind of synthetic method of cefazolin acid

A technology of cefazolin acid and a synthesis method, which is applied in the field of chemical drug synthesis, can solve the problems of low product conversion rate, long process steps, and many use solvents, and achieves high product conversion rate, high product yield, and less use of solvents. Effect

Active Publication Date: 2017-07-04
QILU ANTIBIOTICS PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] One, using 7-aminocephalosporanic acid as a raw material to synthesize an intermediate with thiadiazole and then crystallize the intermediate to synthesize cefazolin acid with tetrazoleacetic acid; as Chinese patent document CN102617607A (application number 201210093006.9) discloses a A method for preparing cefazolin compound, the method needs 7-aminocephalosporanic acid and thiadiazole to synthesize cefazolin acid intermediate in a solvent, and crystallization, resulting in long process steps, many solvents used, and low product yield
[0006] Two, take GCLE as raw material, after connecting thiadiazole, remove the 7-position protecting group of GCLE with enzymatic method, remove carboxylic acid protecting group, react with tetrazolium acetic acid again; As Chinese patent document CN1178220A (application number 96117398.X ) discloses the method for preparing cefazolin, the method step is long, needs to remove two protecting groups and uses many solvents, and the product conversion rate is low

Method used

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  • A kind of synthetic method of cefazolin acid
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  • A kind of synthetic method of cefazolin acid

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Embodiment 1

[0044] The preparation of embodiment 1 cefazolin acid

[0045] A kind of synthetic method of cefazolin acid, comprises the steps:

[0046] (1) Put 150g of dichloromethane and 40.0g (0.147mol) of 7-aminocephalosporanic acid into the reaction flask, cool down to -10~-20°C, slowly add 18.6g (0.162mol) of tetramethylguanidine, and feed liquid Clarify, prepare 7-aminocephalosporanic acid solution, and store it at -20~-30°C for later use;

[0047] (2) Put 150g of dichloromethane and 20.7g (0.162mol) of tetrazoleacetic acid into the reaction bottle, cool down to -10~-20°C, add 16.4g (0.162mol) of triethylamine, cool down to -40~- At 50°C, add 19.5g (0.162mol) of pivaloyl chloride and react for 1 hour to obtain an acid anhydride solution;

[0048] (3) Add the dissolved 7-aminocephalosporanic acid solution prepared in step (1) into the anhydride solution prepared in step (2), react for 1 hour at a temperature of -40 to -50°C, and add 150 g of water Extraction, to prepare the extract...

Embodiment 2

[0050] The preparation of embodiment 2 cefazolin acid

[0051] A kind of synthetic method of cefazolin acid, comprises the steps:

[0052] (1) Put 100g of dichloromethane and 40.0g (0.147mol) of 7-aminocephalosporanic acid into the reaction bottle, cool down to -10~-20°C, slowly add 16.4g (0.162mol) of triethylamine, and the feed liquid is clarified , to prepare a solution of 7-aminocephalosporanic acid, and store it at -20~-30°C for future use;

[0053] (2) Put 100g of dichloromethane and 20.7g (0.162mol) of tetrazoleacetic acid into the reaction bottle, cool down to -10~-20°C, add 16.4g (0.162mol) of triethylamine, cool down to -40~- At 50°C, add 19.5g (0.162mol) of pivaloyl chloride and react for 1 hour to obtain an acid anhydride solution;

[0054] (3) Add the dissolved 7-aminocephalosporanic acid solution prepared in step (1) into the anhydride solution prepared in step (2), react for 1 hour at a temperature of -40 to -50°C, and add 200 g of water Extraction, to prepare ...

Embodiment 3

[0056] The preparation of embodiment 3 cefazolin acid

[0057] A kind of synthetic method of cefazolin acid, comprises the steps:

[0058] (1) Put 200g of dichloromethane and 40.0g (0.147mol) of 7-aminocephalosporanic acid into the reaction flask, cool down to -10~-20°C, slowly add 18.6g (0.162mol) of tetramethylguanidine, and feed liquid Clarify, prepare 7-aminocephalosporanic acid solution, and store it at -20~-30°C for later use;

[0059] (2) Put 200g of dichloromethane and 20.7g (0.162mol) of tetrazoleacetic acid into the reaction bottle, cool down to -10~-20°C, add 16.4g (0.162mol) of triethylamine, cool down to -40~- At 50°C, add 21.5g (0.178mol) of pivaloyl chloride and react for 1 hour to obtain an acid anhydride solution;

[0060] (3) Add the dissolved 7-aminocephalosporanic acid solution prepared in step (1) into the anhydride solution prepared in step (2), react for 1 hour at a temperature of -40 to -50°C, and add 200 g of water Extraction, to prepare the extract...

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Abstract

The invention relates to a synthetic method of cefazolin acid. According to the synthetic method, 7-aminocephalosporanic acid is taken as a raw material, and is reacted with 1H-tetrazole-1-acetic acid in a solvent so as to obtain an intermediate; the intermediate is reacted with 5-mercapto-1-methyltetrazole under base catalysis at solution states without crystallization, washing, and drying so as to obtain cefazolin acid. One-pot method is adopted; the synthetic method is simple; solvent application amount is low; environmental pollution is low; product yield is high; cost is low; and the synthetic method is suitable for industrialized production.

Description

technical field [0001] The invention relates to a synthesis method of cefazolin acid, which belongs to the technical field of chemical drug synthesis. [0002] technical background [0003] Cefazolin (cefazolin), also known as cephalosporin V or cephalosporin V, is the first generation of semi-synthetic cephalosporin antibiotics developed by Fujisawa Pharmaceutical Factory in Japan. It was put into production in Japan in 1971, successfully trial-produced in my country in the late 1970s, and formally produced in 1985. [0004] The main synthetic methods of cefazolin acid are: [0005] One, using 7-aminocephalosporanic acid as a raw material to synthesize an intermediate with thiadiazole and then crystallize the intermediate to synthesize cefazolin acid with tetrazoleacetic acid; as Chinese patent document CN102617607A (application number 201210093006.9) discloses a A method for preparing a cefazolin compound, the method needs to synthesize a cefazolin acid intermediate with ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D501/36C07D501/04
CPCC07D501/04C07D501/36
Inventor 高阳王欣汤沸侯传山王勇进李凤侠单红宾董付敏范美菊
Owner QILU ANTIBIOTICS PHARMA
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