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Synthesis method of cefoxitin sodium

A technology of cefoxitin sodium and a synthetic method, which is applied in the field of synthesis of cefoxitin sodium, can solve the problems of high impurity content, reduced quality, and reduced yield of cefoxitin, so as to achieve stable product quality, reduce side reactions and Hydrolysis, the effect of reducing product impurities

Active Publication Date: 2019-04-19
SHANGHAI NEW ASIA PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0016] And because the existence of above-mentioned several synthetic or post-processing by-products, cause the synthetic cefoxitin containing impurity amount to be too high, and then cause productive rate to reduce or quality reduce

Method used

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  • Synthesis method of cefoxitin sodium
  • Synthesis method of cefoxitin sodium
  • Synthesis method of cefoxitin sodium

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Embodiment 1

[0065] The cefoxitin involved in the present embodiment 1 is synthesized through the following steps:

[0066] Synthesis of S1.7-a-methoxycefalotin cyclohexylamine salt:

[0067] In the flask at room temperature, add 260mL of dichloromethane, 20ml of methanol and 20ml of tetrahydrofuran, add 25g of cephalothinic acid under stirring, cool to -95°C with liquid nitrogen, add the prepared sodium methoxide solution (80ml of methanol and 40ml of dichloromethane , sodium methoxide 15g). Control the temperature at -86~-89°C, drop the temperature to -95°C after adding, add 8g of tert-butyl hypochlorous acid dropwise, drop the temperature to -90°C after the addition, and react for 45 minutes.

[0068] After the reaction was completed, 6 g of sodium metabisulfite was added and stirred for 10 minutes. Add 18ml of 80% acetic acid and heat up to -65°C. Add 300 ml of 10% sodium chloride aqueous solution, stir evenly after adding, and measure the cephalothin residue ≤ 5% by HPLC. Heat the...

Embodiment 2

[0079] The cefoxitin involved in the present embodiment 2 is synthesized through the following steps:

[0080] Synthesis of S1.7-a-methoxycefalotin cyclohexylamine salt:

[0081] In the flask at room temperature, add 260mL of dichloromethane, 20ml of methanol and 20ml of tetrahydrofuran, add 25g of cephalothinic acid under stirring, cool to -95°C with liquid nitrogen, add the prepared sodium methoxide solution (80ml of methanol and 40ml of dichloromethane , sodium methoxide 15g). Control the temperature at -86~-89°C, drop the temperature to -95°C after adding, add 15g of tert-butyl hypochlorous acid dropwise, drop the temperature to -90°C after the addition, and react for 60 minutes. After the reaction was completed, 8 g of sodium metabisulfite was added and stirred for 15 minutes. Add 25ml of 80% acetic acid and heat up to -65°C. Add 300 ml of 10% sodium chloride aqueous solution, stir evenly after adding, and measure the cephalothin residue ≤ 5% by HPLC.

[0082] Heat th...

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Abstract

The invention provides a synthesis method of cefoxitin sodium. The synthesis method is characterized in that cefalotin acid is taken as the raw material to sequentially synthesize 7-a-methoxyl cefalotin cyclohexane salt, 7-a-methoxyl-3-deacetyl cefalotin benzathine salt, and cefoxitin acid to obtain the target product; cefalotin acid reacts with tert.-butyl hypochloric acid to obtain 7-a-methoxylcefalotin cyclohexane salt, and after reactions, the reaction product is purified by a post treatment. The provided synthesis method can largely reduce the happening rate of side reactions, hydrolysis, and degradation, reduces the impurities, improves the product quality, and increases the yield. Moreover, the product quality is stable, the operation is simple, and the synthesis method is suitablefor industrial production.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a synthetic method of cefoxitin sodium. Background technique [0002] 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: [0003] [0004] At present, the synthetic method of cefoxitin reported in the literature is divided into synthetic starting materials, mainly 7-ACA or carboxy-protected 7-ACA as starting materials. This process route has long reaction steps and needs relatively expensive and rare catalysts. There are many side reactions, low yield, high cost, and are not suitable for industrial production; starting with cephamycin C, the raw material of this process route is relatively rare, the reaction route is long, and th...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D501/57C07D501/04
CPCC07D501/04C07D501/57
Inventor 管海英田静杜雯
Owner SHANGHAI NEW ASIA PHARMA
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