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A kind of ceftezole acid acylation reaction process

A technology for acylation reaction of oxazole acid and acylation reaction, which is applied in the technical field of acylation reaction of ceftizole acid, can solve the problems of low yield, high cost, pollution and the like, achieves simple process route, simple and convenient operation, and solves technical problems Effect

Active Publication Date: 2020-06-09
SHANDONG LUOXIN PHARMA GRP CO LTD +2
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This acid chloride method will cause pollution to the environment, high cost and low yield
[0005] Synthesis process 2: 7-ACA is used as the starting material, under the catalysis of DCC, reacts with 1H-tetrahydroxazole acetic acid to produce 7-(1H tetrazolium acetamido) cephalosporanic acid, and then reacts with 2-mercapto-1 , 3,4-thiadiazole reacts to generate ceftezole acid, the route is simple, but the yield is low, the total yield is only 18.3%

Method used

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  • A kind of ceftezole acid acylation reaction process
  • A kind of ceftezole acid acylation reaction process
  • A kind of ceftezole acid acylation reaction process

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Embodiment

[0025] The preparation process of intermediate 1:

[0026] 2-Mercapto-1,3,4-thiadiazole, BF 3 - Add 100L of dimethyl carbonate and dichloromethane to reactor A, then slowly add 7-ACA, control the reaction temperature at 20-30°C, start the stirring device to carry out the stirring reaction for 5-6h, add hydrochloric acid during the reaction to adjust the pH to 3.5, and the reaction is complete Afterwards, transfer to the water phase, add sodium carbonate to carry out crystallization, centrifuge, and dry to obtain intermediate 1, the resulting product yield, purity and reaction conditions acidic species corresponding relationship are shown in the following table 1, all the intermediates of gained are used with acetonitrile 50L and 30LDMF to dissolve completely, for the next reaction.

[0027] Acylation process of ceftezole acid:

[0028] Step a: Add 12.8kg (100mol) of tetrazoleacetic acid, 150mol of 4-picoline and 100L of dichloromethane into reactor B, control the temperature...

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Abstract

Belonging to the field of medical technology, the invention discloses a ceftezole acid acylation reaction process. The method includes: subjecting pre-prepared intermediate 1 and intermediate 2 to acylation reaction at low temperature. An acylation reaction device adopted by the invention is mainly composed of a stirring unit, a cooling coil, a stirring paddle, an electromagnetic valve, a controller and a temperature sensor. The acylation reaction process provided by the invention is simple, achieves accurate control of the reaction temperature, increases the product yield, and reduces by-product generation.

Description

technical field [0001] The invention relates to the field of drug synthesis, in particular to a ceftezole acid acylation process. Background technique [0002] Ceftezole acid, the chemical name is (6R)-8-oxo-7-[(1H-1-tetrazolylacetyl)amino]-3-[[2-(1,3,4-thia Diazolyl)thio]methyl]-5-thia-1-azabicyclo[4,2,0]oct-2-ene-2-carboxylic acid, synthesized and developed by Japan Fujisawa Pharmaceutical Co. Semi-synthetic cephalosporin antibiotic, marketed in April 1978 under the trade name Ceolslin. The application of this drug in our country is relatively late. In 2002, Harbin Pharmaceutical and Tianjin Xinfeng produced raw materials and preparations. In recent years, the annual growth rate of the usage is 399%. This product is mainly used to treat infections caused by Staphylococcus aureus, Streptococcus pyogenes, Pneumococcus, Escherichia coli, Klebsiella pneumoniae, etc., such as secondary infections of the chronic respiratory system caused by sepsis, pneumonia, bronchitis, and b...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D501/36C07D501/06
CPCC07D501/06C07D501/36
Inventor 朱玉青程明李公存
Owner SHANDONG LUOXIN PHARMA GRP CO LTD
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