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Preparation method of (Z)-2-(tert-methoxycarbonyl methoxyimino)-2-(2-aminothiazol-4-yl)acetic acid

A technology of cefixime side chain acid and cefixime ring-opening side chain acid, applied in the direction of organic chemistry, etc., can solve problems such as hidden dangers of production safety, increase process flow, increase production cost, etc. The effect of simple handling and lower production costs

Inactive Publication Date: 2017-05-10
河北合佳医药科技集团股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Cefixime side chain acid is an important intermediate for the synthesis of cefixime antibiotics, and the synthesis of cefixime side chain acid in the existing technology is usually by cefixime ring-opening side chain acid and thiourea in methanol-water solution And in the presence of acid-binding agents sodium acetate and sodium bicarbonate, it is prepared by ring-closing reaction. In this reaction, methanol, an organic solvent, needs to be used, and higher safety measures must be equipped for the storage and use of methanol in production, and In the production process, methanol needs to be recovered, which not only increases the process flow but also increases the production cost, and there are hidden dangers in production safety

Method used

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  • Preparation method of (Z)-2-(tert-methoxycarbonyl methoxyimino)-2-(2-aminothiazol-4-yl)acetic acid
  • Preparation method of (Z)-2-(tert-methoxycarbonyl methoxyimino)-2-(2-aminothiazol-4-yl)acetic acid

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Embodiment

[0021] This embodiment relates to a method for preparing cefixime side chain acid, including the following steps:

[0022] Cefixime ring-opening side chain acid is prepared by laboratory synthesis reaction. Using tert-butyl acetoacetate as raw material, cefixime ring-opening side chain acid is synthesized through oximation, alkylation, and chloro-acid hydrolysis. The purity is greater than 92. %;

[0023] a. In a 500ml four-necked bottle, add 150g water and 100g cefixime ring-opening side chain acid successively, control the temperature at 15~20℃, and slowly add ammonium bicarbonate until the cefixime ring-opening side chain acid is dissolved, and then use Adjust the pH value of ammonium bicarbonate to 4.5±0.2, then add activated carbon for decolorization, stir at 15°C for 30 minutes, and filter to obtain the ammonium salt aqueous solution of cefixime ring-opening side chain acid; the amount of ammonium bicarbonate added in this step is 30.67g;

[0024] b. Add 34.6g of thiourea, 230...

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Abstract

The invention relates to a preparation method of (Z)-2-(tert-methoxycarbonyl methoxyimino)-2-(2-aminothiazol-4-yl)acetic acid. A step that 4-chioro-2-(Z)-methoxycarbonyl methoxyimino-3-oxobutyric acid reacts with thiourea in a water-phase solution to make the (Z)-2-(tert-methoxycarbonyl methoxyimino)-2-(2-aminothiazol-4-yl)acetic acid is set. According to the preparation method of the (Z)-2-(tert-methoxycarbonyl methoxyimino)-2-(2-aminothiazol-4-yl)acetic acid obtained by the preparation method, a reaction carried out in the water-phase solution is adopted; the use of an organic solvent is not needed; further, the post treatment of a product is simply operated; the procedure of recovering the solvent does not need to be carried out; the production yield of the product can be improved; the production cost is decreased; the obvious economic benefit is brought about; moreover, the preparation method has positive effects in the aspects of safety in production and the influence on a production environment, and is suitable for large-scale industrial application.

Description

Technical field [0001] The invention relates to the technical field of the synthesis of cefixime side chain acids, in particular to a method for preparing cefixime side chain acids. Background technique [0002] Cefixime is a third-generation oral cephalosporin antibiotic drug. Studies in vivo and in vitro have shown that the drug has a broad antibacterial spectrum, against Streptococcus pyogenes, pneumococcus, Streptococcus agalactiae, Neisseria gonorrhoeae, Influenza bacillus, Moracatra and Escherichia coli Most Enterobacteriaceae such as Pneumoniae and Pneumoniae have good antibacterial activity, strong antibacterial effect, and strong stability to the β-lactamase produced by the bacteria, so they are widely used in clinical medicine. [0003] Cefixime side chain acid is an important intermediate for the synthesis of cefixime antibiotics, and the synthesis of cefixime side chain acid in the existing technology is usually by cefixime ring-opening side chain acid and thiourea in m...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D277/593
CPCC07D277/593
Inventor 刘振强董永利单国申王荣霞臧传梅
Owner 河北合佳医药科技集团股份有限公司
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