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Synthesis method of cefradine

A synthesis method and technology of cefradine, applied in the field of drug synthesis, can solve the problems of reducing the harshness of the reaction, harsh reaction conditions of cefradine, difficult to control, etc., and achieve the effects of reducing the harshness of the reaction, reducing the intake of impurities, and accelerating the recycling and utilization.

Pending Publication Date: 2022-07-05
ZHEJIANG ZHEBANG PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Aiming at the problems in the prior art, the present invention provides a synthetic method of cephradine, which solves the problem that the reaction conditions of cephradine are harsh and difficult to control, utilizes an immobilized reaction system to form a mixed anhydride, effectively controls the acylation temperature, and reduces the harshness of the reaction

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] A method for synthesizing cefradine, the sodium salt is used as a raw material, an acylation reaction is carried out with pivaloyl chloride, 7-ADCA and tetramethylguanidine are dissolved in dichloromethane to form a salt solution, and the acylation product and the salt solution are carried out. Condensation reaction, the obtained product is hydrolyzed and stratified under acidic conditions, crystallized and centrifuged to obtain the product; and the temperature of the acylation reaction is -30°C.

[0023] The specific steps of the synthetic method are as follows:

[0024]Step 1, acylation reaction: under nitrogen protection, the temperature is controlled to -30°C, dichloromethane is injected into the acylation kettle, and then the catalyst and D-dihydrophenylglycine sodium salt are added, and the temperature is raised to -14°C. Under the temperature, add pivaloyl chloride quickly to carry out the acylation reaction, and after the reaction is completed, the temperature i...

Embodiment 2

[0033] A method for synthesizing cefradine, the sodium salt is used as a raw material, an acylation reaction is carried out with pivaloyl chloride, 7-ADCA and tetramethylguanidine are dissolved in dichloromethane to form a salt solution, and the acylation product and the salt solution are carried out. Condensation reaction, the obtained product is hydrolyzed and stratified under acidic conditions, crystallized and centrifuged to obtain the product; and the temperature of the acylation reaction is -30°C.

[0034] The specific steps of the synthetic method are as follows:

[0035] Step 1, acylation reaction: under nitrogen protection, the temperature is controlled to -30°C, dichloromethane is injected into the acylation kettle, and then the catalyst and D-dihydrophenylglycine sodium salt are added, and the temperature is raised to -14°C. Under the temperature, add pivaloyl chloride quickly to carry out the acylation reaction, and after the reaction is completed, the temperature ...

Embodiment 3

[0044] A method for synthesizing cefradine, the sodium salt is used as a raw material, an acylation reaction is carried out with pivaloyl chloride, 7-ADCA and tetramethylguanidine are dissolved in dichloromethane to form a salt solution, and the acylation product and the salt solution are carried out. Condensation reaction, the obtained product is hydrolyzed and stratified under acidic conditions, crystallized and centrifuged to obtain the product; and the temperature of the acylation reaction is -30°C.

[0045] The specific steps of the synthetic method are as follows:

[0046] Step 1, acylation reaction: under nitrogen protection, the temperature is controlled to -30°C, dichloromethane is injected into the acylation kettle, and then the catalyst and D-dihydrophenylglycine sodium salt are added, and the temperature is raised to -14°C. Under the temperature, add pivaloyl chloride quickly to carry out the acylation reaction, and after the reaction is completed, the temperature ...

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PUM

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Abstract

The invention belongs to the field of medicine synthesis, and particularly relates to a synthesis method of cefradine, which comprises the following steps: by taking Dane sodium salt as a raw material, carrying out acylation reaction with pivaloyl chloride, dissolving 7-ADCA and tetramethylguanidine in dichloromethane to form a salt dissolving solution, carrying out condensation reaction on an acylation product and the salt dissolving solution, hydrolyzing and layering the obtained product under an acidic condition, and separating out a solid product, thereby obtaining the cefradine. Crystallizing and centrifuging to obtain a product; the temperature of the acylation reaction is-30 DEG C. The method solves the problem that cefradine reaction conditions are harsh and are difficult to control, mixed anhydride is formed by utilizing an immobilized reaction system, the acylation temperature is effectively controlled, and the reaction harsh is reduced.

Description

technical field [0001] The invention belongs to the field of drug synthesis, in particular to a method for synthesizing cefradine. Background technique [0002] Cefradine is the first-generation injection or oral cephem β-lactam antibiotic drug, the main drug has strong bactericidal effect on drug-resistant Staphylococcus aureus and Klebsiella pulmonary Pneumococcus, Escherichia coli, and some Proteobacteria all have antibacterial effects, and have the advantages of broad antibacterial spectrum, strong bactericidal power, small allergic reaction, and high stability to β-lactamase. Clinically, it is mainly used to treat infections of the respiratory tract, urinary tract, skin and soft tissue. [0003] The current industrial production is mainly based on chemical synthesis, which is formed by condensation, hydrolysis and crystallization of protected 7-ADCA and dihydrophenylglycine sodium salt through the mixed acid anhydride prepared from pivaloyl chloride. However, in this ...

Claims

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Application Information

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IPC IPC(8): C07D501/22C07D501/06C07D501/04
CPCC07D501/22C07D501/06C07D501/04Y02P20/584
Inventor 胡宇超潘高娜王志勇金飞标袁亚敏
Owner ZHEJIANG ZHEBANG PHARMA