Antibacterial drugs cefoxitin preparation process

Abstract

The invention provides a method for preparing cefoxitin (I). It comprises taking 7 alpha- methoxy- 7 beta- aminocephalosporanic acid (7- MAC) as raw material, carrying out 2- thiofuran acetylation reaction, hydrolytic reaction, carbamylation reaction and getting cefoxitin (I). The invention greatly increases the prductivity for cefoxitin and its sodium salt and reduces production cost.

Description

technical field The invention relates to a preparation method of a compound, in particular to a preparation method of a cephalosporin. Background technique Cefoxitin (Cefoxitin,), the chemical name is (6R, 7S)-3-carbamoyloxymethyl-7-methoxy-8-oxo-7-[2-(2-thienyl)acetamido ]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid is a semi-synthetic cephamycin antibiotic developed by Merck Company of the United States. Its chemical structural formula (I) is as follows: Clinically, the sodium salt of cefoxitin is used to make injections for the treatment of bacterial infections. The drug was first approved for marketing by Japan's Daiichi Pharmaceutical Development Company in August 1979 under the trade name Cenomycin. The antibacterial effect of cefoxitin is similar to that of the second-generation cephalosporins, but because its structure contains a 7α-methoxy group, it greatly reduces the hydrolytic damage of β-lactamase in bacteria, and its drug resistance Much less o...

AI Technical Summary

Problems solved by technology

The actual production has very strict requirements on the reaction conditions, and the production cost is high

Orchid company (Deshpande et al., WO2004083217) omits the protection and deprotection of carboxyl group, directly uses sodium methylate or lithium methylate etc. as strong base, and uses NCS or tert-butyl hypochlorite etc. as reagents at -90°C. The 7-position introduces a methoxyl group, and obtains II in one step, but the yield is low

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