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Method for synthesizing cefoxitin acid

A technology of cefoxitin acid and a synthesis method, which is applied in the field of synthesis of cefoxitin acid, can solve the problems of high cost of cefoxitin acid, reduced yield and the like, and achieves the advantages of reducing production steps, reducing production cost and low impurity content. Effect

Inactive Publication Date: 2016-03-09
四川清山绿水医药化工股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the existing technology, the cost of cefoxitin acid is high, the first decolorization is water phase decolorization, and a phase inversion is required before decolorization, which reduces the yield of the final product

Method used

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  • Method for synthesizing cefoxitin acid
  • Method for synthesizing cefoxitin acid
  • Method for synthesizing cefoxitin acid

Examples

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Effect test

Embodiment 1

[0022] see figure 1 , in the embodiment of the present invention, a kind of synthetic method of cefoxitin acid, the steps are:

[0023] Use 7-aminocephalosporanic acid as raw material, add protective agents such as trimethylchlorosilane or BSA respectively, add sodium methoxide and tert-butyl hypochlorite after protection, and the molar ratio of 7-aminocephalosporanic acid to sodium methoxide 1:1. Under the catalytic condition of tert-butyl hypochlorite, react with sodium methoxide, the reaction temperature is -95°C, introduce a methoxyl group at the 7-position of 7-aminocephalosporanic acid to obtain a methoxyl compound, and the reaction ends after 50 minutes. Add 2-thiopheneacetyl chloride dropwise to react, then add deacylase to the obtained wet material in alkaline solution for hydrolysis, the hydrolysis temperature is 20°C, the hydrolysis time is 30min, after hydrolysis, filter out the acylase; after the reaction is completed, cool down to room temperature , drip benzat...

Embodiment 2

[0027] In the embodiment of the present invention, a kind of synthetic method of cefoxitin acid, the steps are:

[0028] Use 7-aminocephalosporanic acid as raw material, add protective agents such as trimethylchlorosilane or BSA respectively, add sodium methoxide and tert-butyl hypochlorite after protection, and the molar ratio of 7-aminocephalosporanic acid to sodium methoxide It is 1:2. Under the catalytic condition of tert-butyl hypochlorite, react with sodium methoxide, the reaction temperature is -60°C, introduce a methoxyl group at the 7-position of 7-aminocephalosporanic acid to obtain a methoxyl compound, and the reaction ends after 60 minutes. Add 2-thiophene acetyl chloride dropwise to react, then add deacylase to the obtained wet material in alkaline solution for hydrolysis, the hydrolysis temperature is 25°C, the hydrolysis time is 40min, after hydrolysis, filter out the acylase; after the reaction is completed, cool down to room temperature , drip benzathine diac...

Embodiment 3

[0032] In the embodiment of the present invention, a kind of synthetic method of cefoxitin acid, the steps are:

[0033] Use 7-aminocephalosporanic acid as raw material, add protective agents such as trimethylchlorosilane or BSA respectively, add sodium methoxide and tert-butyl hypochlorite after protection, and the molar ratio of 7-aminocephalosporanic acid to sodium methoxide It is 1:1.5. Under the catalytic condition of tert-butyl hypochlorite, react with sodium methoxide, the reaction temperature is -55°C, introduce a methoxyl group at the 7-position of 7-aminocephalosporanic acid to obtain a methoxyl compound, and the reaction ends after 55 minutes. Add 2-thiopheneacetyl chloride dropwise for reaction, then add deacylase to the obtained wet material in alkaline solution for hydrolysis, the hydrolysis temperature is 30°C, the hydrolysis time is 35min, after hydrolysis, filter out the acylase; after the reaction is completed, cool down to room temperature , drip benzathine...

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Abstract

The invention discloses a method for synthesizing cefoxitin acid. 7-aminocephalosporanic acid is adopted as a raw material and reacts with sodium methylate under protection of a protection agent, methoxy is introduced into the seventh bit of 7-aminocephalosporanic acid, and methoxide complex is obtained; after the reaction is finished, 2-thiophene acetyl chemical reagent is dropwise added for reacting, then solidifying enzyme is added to obtained wet feed in an alkaline solution for hydrolysis, and after hydrolysis is completed, solidifying enzyme is filtered out; after the reaction is finished, a benzathine diacetate water solution is dropwise added to reaction liquid, crystals are separated out, and a compound I is obtained; the compound I and an ammonia methoxyl acylation reagent act, a carbamyl methoxyl group is introduced to the third bit of the compound I, and cefoxitin acid is obtained. The synthesis process is simple, the steps are easy and convenient, implementation is easy, the yield is effectively increased, production cost is reduced, the production steps are reduced, the obtained product is high in purity, the impurity content is low, the color gradation is good, product quality is effectively improved, drug use safety is improved, and the method is suitable for mass production.

Description

technical field [0001] The invention relates to the technical field of drug synthesis, in particular to a method for synthesizing cefoxitin acid. Background technique [0002] Cefoxitin acid, the chemical name is (6R,7S)-3-carbamoyloxymethyl-7-methoxy-8-oxo-7-(2-(2-thiazolyl)acetamide base)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid. Cefoxitin acid is a semi-synthetic cefoxitin antibiotic developed by MercK in the United States. Its sodium salt, cefoxitin sodium, has a balanced antibacterial spectrum and is stable to β-lactamase. At present, there is a relatively serious abuse of antibiotics, which has gradually increased the resistance of antibiotics, and the resistance of bacteria has constituted a serious threat to β-lactam antibiotics. The hydrolytic ring opening under the action of β-lactamase is the main reason for the inactivation of these antibiotics. Cefoxitin, as a second-generation cephalosporin, has once again attracted people's attention because of...

Claims

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Application Information

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IPC IPC(8): C12P35/08C07D501/57C07D501/04
CPCC12P35/08C07D501/04C07D501/57
Inventor 梁建中朱昌凡卢祖强
Owner 四川清山绿水医药化工股份有限公司
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