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Cefazedone synthesis method

A synthesis method and a technology for cefoxidone, which are applied in the field of drug synthesis, can solve the problems of affecting the total yield and product quality of the product, being difficult to remove, and having many side reactions, so as to improve the total yield and purity of the product, the route is simple, and the product high yield effect

Active Publication Date: 2019-12-13
SHANDONG LUOXIN PHARMA GRP HENGXIN PHARMA CO LTD +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] There are many side reactions in the synthesis process of the above route and are difficult to remove, which affects the total yield and product quality of the product.

Method used

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  • Cefazedone synthesis method
  • Cefazedone synthesis method

Examples

Experimental program
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Effect test

Embodiment 1

[0025] Preparation of compound Ⅲ

[0026] Dissolve boron trifluoride-dimethyl carbonate complex (2mol) in 150ml of dimethyl carbonate, then add 132.25g (1mol) of compound II, stir and dissolve at room temperature, and control the temperature at 0-5°C. Add formic acid (1mol), then slowly add 272.30g (1mol) of 7-ACA dropwise, control the reaction at 0-5°C for 1-1.5h, transfer to water, adjust the pH to 3.8 with ammonia water, precipitate crystals, grow crystals for 1h, It was filtered, washed with purified water, and vacuum-dried to obtain 20.32 g of compound III, with a molar yield of 93%, a purity of 99.3%, and a maximum of 0.07%.

Embodiment 2

[0028] Preparation of compound Ⅲ

[0029] Dissolve boron trifluoride-dimethyl carbonate complex (2.5mol) in 150ml of dimethyl carbonate, then add 132.26g (1mol) of compound II, stir and dissolve at room temperature, and control the temperature at 5-10°C , add glacial acetic acid (1mol), then slowly add 7-ACA 299.51g (1.1mol) dropwise, control the reaction at 5-10°C for 1-1.5h, transfer to water, adjust the pH to 3.8 with ammonia water, precipitate crystals, and raise After 1 hour of crystallization, filtered, washed with purified water, and vacuum-dried to obtain 327.21 g of compound III, the molar yield was 95%, the purity was 99.4%, and the maximum monoheterogeneity was 0.08%.

Embodiment 3

[0031] Preparation of compound Ⅲ

[0032] Dissolve boron trifluoride-dimethyl carbonate complex (2mol) in 150ml of dimethyl carbonate, then add 132.26g (1mol) of compound II, stir and dissolve at room temperature, and control the temperature at 10-15°C. Add formic acid (1mol), then slowly add 272.29g (1mol) of 7-ACA dropwise, control the reaction at 10-15°C for 1-1.5h, transfer to water, adjust the pH to 3.8 with ammonia water, precipitate crystals, grow crystals for 1h, It was filtered, washed with purified water, and vacuum-dried to obtain 296.21 g of compound III, with a molar yield of 86%, a purity of 98.7%, and a maximum of 0.23%.

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Abstract

The invention discloses a cefazedone synthesis method. A compound II reacts with 7-ACA to prepare a compound III, and the compound III reacts with a compound IV to prepare the final product cefazedone. The method has the advantages of simple reaction process, easiness in operation, high total yield and high purity of the product, few byproducts, and suitableness for industrial production.

Description

technical field [0001] The invention belongs to the technical field of drug synthesis, in particular to a method for synthesizing cefazedone. Background technique [0002] Cefazedone was developed by E Merck, Darmstadt laboratory in the late 1970s and is the first generation of cephalosporin antibiotics. In 1979, Merck was the first to go public in Germany, and then it was listed in neighboring countries, South Korea, Romania, Taiwan Province of China and other countries and regions. Cefozione is a semi-synthetic cephalosporin antibiotic that inhibits and kills bacteria mainly by interfering with and preventing the synthesis of bacterial cell walls. It has good antibacterial activity against common clinical Gram-positive and some Gram-negative bacteria, and some anaerobic bacteria, and can be used for respiratory system, urinary system, gastrointestinal tract infection, gynecology, peritoneum, skin, soft tissue and plastic surgery, etc. Sensitivity to the treatment of both...

Claims

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Application Information

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IPC IPC(8): C07D501/36C07D501/18C07D501/06C07D501/04
CPCC07D501/36C07D501/18C07D501/06C07D501/04Y02P20/55
Inventor 刘振腾梁振刘江刘庆利张继文
Owner SHANDONG LUOXIN PHARMA GRP HENGXIN PHARMA CO LTD
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