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Preparation method of 7-amino-3-chloro-3-cephem-4-carboxylic acid

A technology of cephalosporin and carboxylic acid, applied in the direction of organic chemistry, etc., can solve the problems of increased yield, long reaction time, and increased cost, and achieve the effects of short reaction time, low cost, and energy saving

Inactive Publication Date: 2014-04-02
河北爱弗特精细化工有限责任公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] In this process route, triphosgene is used in the chlorination link, but the reaction time is long and the cost is increased; in the phenylacetyl removal link, penicillin G acylase is used, but the yield needs to be increased

Method used

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  • Preparation method of 7-amino-3-chloro-3-cephem-4-carboxylic acid

Examples

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example 1

[0019] At a temperature of 20-25°C, add 60mL of dehydrated dimethylformamide to an empty container, then add 7g of thionyl chloride, control the temperature at 25-30°C, and stir for one hour; then add 120mL of dehydrated dimethylformamide Phenyl formamide and 18g of 7-phenylacetamido-3-hydroxyl-3-cephalosporin-4-carboxylic acid diphenylmethyl ester were added to another empty container, the temperature was controlled at 20-25°C, stirred and dissolved, and the previously prepared Add dimethylformamide and thionyl chloride solution to this solution, add 168 mg dimethyl sulfone at the same time, cool down, control the temperature at 25 ° C, stir for 6 hours, add 1.5 liters of ice water to cool down, and filter the separated solid. Rinse with a small amount of water, and then vacuum-dry to obtain 17.36 g of 7-phenylacetamido-3-chloro-3-cephradine-4-carboxylic acid diphenylmethyl ester.

[0020] Add the prepared 17.36g of 7-phenylacetamido-3-chloro-3-cephalosporin-4-carboxylic acid...

example 2

[0023] At a temperature of 20-25°C, add 2000mL of dehydrated dimethylformamide into an empty container, add 78g of thionyl chloride at room temperature, control the temperature at 30°C, stir for one hour, then add 1900mg of dimethyl sulfone and 200g 7-phenylacetamido-3-hydroxyl-3-cephine-4-carboxylic acid diphenylmethyl ester, control the temperature at 25°C, stir for 7 hours, add 15 liters of ice water, filter the separated solid, and use a small amount of Rinse with water, and then dry in vacuo to obtain 184.26 g of 7-phenylacetamido-3-chloro-3-cephalosporin-4-carboxylic acid diphenylmethyl ester.

[0024] Add 184.26g of 7-phenylacetamido-3-chloro-3-cephine-4-carboxylic acid diphenylmethyl ester and 960mL of p-cresol to the empty flask, control the temperature at 45-50°C, and stir the reaction for half hour, add 1900mL ethyl acetate and 3800mL 5% sodium bicarbonate aqueous solution for extraction, the extracted water layer is extracted three times with 2760mL ethyl acetate, ...

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Abstract

The invention relates to a preparation method of 7-amino-3-chloro-3-cephem-4-carboxylic acid. The preparation method takes 7-phenacetylamino-3-hydroxyl-3-cephem-4-diphenylmethyl carboxylate as a starting material and comprises the following steps: (1) chloridizing the starting material to obtain 7-phenacetylamino-3-chloro-3-cephem-4-diphenylmethyl carboxylate; (2) removing diphenylmethyl on the C-4 site to obtain 7-phenacetylamino-3-chloro-3-cephem-4-carboxylic acid; (3) removing phenylacetyl on the C-7 site to obtain 7-amino-3-chloro-3-cephem-4-carboxylic acid. In the whole process route, the reaction conditions are mild; the raw materials are cheap and easy to obtain; severe harmful substances are not used; the preparation method is low in pollution, saves resources, and is high in product yield, low in cost and suitable for industrial production.

Description

technical field [0001] The invention relates to a method for preparing 7-amino-3-chloro-3-cephalosporin-4-carboxylic acid, 7-amino-3-chloro-3-cephalosporin-4-carboxylic acid is used to prepare cephalosporin antibiotic cephalosporin Crowe's key core, referred to as 7-ACCA. Cefaclor is an oral broad-spectrum cephalosporin antibiotic with good curative effect, safety and low allergenicity. Background technique [0002] Because of its good curative effect, safety and low allergenicity, cefaclor is suitable for all kinds of people and is known as a children's antibiotic. At present, my country's cefaclor mainly relies on imports, and the domestic output is not high. Batch production has restricted the development of cefaclor production. Preparation of 7-amino-3-chloro-3-cephalosporin-4-carboxylic acid is mainly based on 7-phenylacetamido-3-hydroxyl-3-cephalosporin-4-carboxylic acid benzhydryl ester or 7-phenylacetamido- 3-Hydroxy-3-cephine-4-carboxylic acid p-nitrobenzyl ester...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D501/59C07D501/04
CPCC07D501/59C07D501/04
Inventor 邵天邵新生
Owner 河北爱弗特精细化工有限责任公司
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