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Method for preparing cefoxitin sodium

A technology of cefoxitin sodium and cefoxitin acid is applied in the directions of organic chemistry, anti-infective drugs, drug combinations, etc., to achieve the effects of reducing production costs, improving product yield, and simplifying production steps

Active Publication Date: 2011-06-01
哈药集团股份有限公司 +1
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The disadvantage of this method is the need to use highly toxic thallium salts

Method used

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  • Method for preparing cefoxitin sodium
  • Method for preparing cefoxitin sodium
  • Method for preparing cefoxitin sodium

Examples

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Embodiment 1

[0041] Preparation of deacetylthiophene acid I

[0042] At room temperature, add 120 g of deacetylated 7-ACA into a mixed solution of 1.2 L of acetone and 0.6 L of water, stir rapidly, add 70 g of thiophene acetyl chloride dropwise, and react for 30 minutes after the drop is complete, evaporate the acetone in vacuum at 40°C, and the remaining 0.7L concentrate. Add 10% HCL dropwise to the concentrated solution at room temperature to stabilize the pH value at 2.5, grow the crystal for 30 minutes, filter with suction, wash the filter cake three times with 0.9L of water, and dry it under vacuum at 30°C. Get deacetylthiophene acid 158g, yield 131.7%

[0043] Intermediate (6R, 7S)-3-carbamoylmethoxy-7-[2-(2-thienyl)acetamido]-8-oxo-5-thia-1-azabicyclo[4.2. 0] Preparation of Oct-2-ene-2-carboxylic acid II

[0044] At minus 30°C, add 150 g of deacetylthiophene acid into 1 L of tetrahydrofuran, and stir until completely dissolved. Add 72 g of carbamyl reagent (chlorosulfonyl isocya...

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Abstract

The invention provides a method for preparing cefoxitin sodium, which comprises the following steps: 1, using deacetyl7-ACA as a raw material, and introducing thiopheneacetyls to obtain an deacetylthiophene acid I; 2, introducing carbamoymethoxyls to the positions 3 of molecules of deacetylthiophene acid I to obtain an intermediate of (6R, 7S)-3-carbamoymethoxyl-7-[2-(2-theiophene) acetamino]-8-oxo-5-thia-1-azabicyclo[4.2.0]octa-2-en-2-methanoic acid II; 3, reacting the intermediate II with lithium methoxide to introduce methoxyls into positions 7 of the molecules of the intermediate to obtain cefoxitin acid III; and 4, adding ethanol solution of a sodium salt into an organic solvent containing the cefoxitin acid and obtaining the cefoxitin sodium IV through suction filtration and drying.

Description

technical field [0001] The invention relates to a preparation method of a compound, in particular to a preparation method of cefoxitin sodium. Background technique [0002] Cefoxitin sodium, chemical name: (6R, 7S)-3-carbamoyloxymethyl-7-methoxy-8-oxo-7-[2-(2-thiazolyl) ) Acetamido]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid sodium salt. Its chemical structural formula is as follows: [0003] [0004] It is a second-generation cephalosporin antibiotic developed by Merck Company of the United States. It has a balanced antibacterial spectrum and is stable to β-lactamase. At present, due to the increasing bacterial resistance to cephalosporins, cefoxitin, which is different from the first-generation and third-generation cephalosporins, has once again attracted people's attention. [0005] Compared with the cephalosporin ring 7-ACA, the structure that needs to be changed in the synthesis of cefoxitin has three parts: the 3-position acetoxymethyl group is replace...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D501/57C07D501/06A61P31/00
Inventor 马杰赵玉新景士云黄宇红杨洋杨松高晶胡明张丽君
Owner 哈药集团股份有限公司
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