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Cephalo olefine onium salt compound and its preparing method, and method for synthesizing cephalo pyoxime with said compound

A technology of cephems and compounds, which is applied in the field of synthesizing cefepime hydrochloride, can solve problems such as high cost, and achieve the effects of simple reaction route, reduced production cost, and mild reaction conditions

Inactive Publication Date: 2003-01-22
TIANJIN INSTITUTE OF PHARMA RESEARCH
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  • Abstract
  • Description
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Problems solved by technology

This method requires penicillin G acylase to participate in the biological cleavage process, and the penicillin G acylase used needs to maintain its activity for recycling, otherwise it will cause higher costs

Method used

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  • Cephalo olefine onium salt compound and its preparing method, and method for synthesizing cephalo pyoxime with said compound

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Embodiment Construction

[0024] The present invention will be further described below in conjunction with embodiment:

[0025] 1. Preparation of 7β-formamido-3-chloromethyl-3-cephem-4-carboxylic acid p-methoxybenzyl ester (III):

[0026] Take 60g of 7β-amino-3-chloromethyl-3-cephem-4-carboxylic acid p-methoxybenzyl ester hydrochloride (II) and 120ml of tetrahydrofuran, add them to a 250ml reaction flask in turn, and drop them under ice bath Add 20.5ml of triethylamine, after dropping, remove the ice bath, stir at room temperature for 1 hour, filter, wash with 60ml of tetrahydrofuran three times, and set the filtrate for use.

[0027] In another 250ml reaction bottle, add 27.3ml of formic acid and 68.4ml of acetic anhydride, stir and react at 40-50°C for 1 hour, filter, pour the above-mentioned filtrate into it, and precipitate light yellow crystals, continue to react at 45°C and keep warm After 1 hour, cool down, stir in an ice bath for 1 hour, filter, and wash with ethanol to obtain 38.1 g of white ...

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Abstract

The present invention relates to 7beta-alkylamido-3-(1-methyl-1-pyrrolidyl onium) methyl-3-cephalo olefine-4-carboxylate and its preparation process and the synthesizing process of cephalo pyroxime hydrochloride with the said intermediate. The present invention has mild reaction condition, no need of expensive reagent and benzyl penicillin acylase, low cost, high product purity, and simple and practical reaction path.

Description

technical field [0001] The invention relates to an intermediate of cephalosporin antibiotics, a synthesis method thereof and a method for synthesizing cefepime hydrochloride with the intermediate. Background technique [0002] U.S. Patent No. 4,868,294 and U.S. No. 4,714,760 etc. disclose the preparation method of cefepime hydrochloride, they all need to be raw material with 7-amino-3-acetoxymethyl cephalosporanic acid (7-ACA), through generating silicon compound intermediate However, the preparation of these silicon compound intermediates often requires the use of special reagents such as iodotrimethylsilane and 1,1,2-trichlorotrifluoroethane. [0003] U.S. Patent No. 4,406,899 discloses another method for preparing cefepime hydrochloride, which uses 7-phenylacetamido-3-chloromethyl cephalosporanic acid benzhydryl ester as raw material, at first with N-methylpyrrolidine , react in the presence of NaI to obtain a 3-position substituent, then car...

Claims

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Application Information

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IPC IPC(8): C07D501/48
Inventor 孟红赵平王学知刘志友张建宾
Owner TIANJIN INSTITUTE OF PHARMA RESEARCH
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