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Method for preparing cefoxitin acid

A technology of cefoxitin acid and thiophene acid, which is applied in the field of medicine, can solve the problems of increasing production costs and production costs, and achieve the effects of eliminating low-temperature strong alkali hydrolysis, improving product quality, and avoiding side reactions

Active Publication Date: 2013-08-14
重庆天地药业有限责任公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

This undoubtedly increases the production cost process and production cost

Method used

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  • Method for preparing cefoxitin acid
  • Method for preparing cefoxitin acid
  • Method for preparing cefoxitin acid

Examples

Experimental program
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Effect test

Embodiment 1

[0026] Embodiment 1: the preparation of methoxycephalosporin (2)

[0027] Add 100g of cefalotin sodium into a mixed solvent of 500ml of dichloromethane and 100ml of methanol, add 15g of methanesulfonic acid and stir to dissolve. After the above reaction solution is completely dissolved, cool the reaction solution to -90°C, add 50ml of dichloromethane dissolved in 30g of N-chlorosuccinimide, keep it warm at -90°C, and slowly add it dropwise to -10-- Use 450ml of 20% sodium methoxide at 15°C to keep the temperature of the reaction solution stable at -85--90°C, and wash the dropper with 15ml of methanol after dropping. After reacting for 1 hour, add 15g of N-chlorosuccinimide, continue to react for 2 hours, add 21g of stopper, continue to react for 10 minutes, add 150g of 80% acetic acid at -75-78°C, and use 10% of chlorine respectively Wash 3 times with 500 ml of sodium chloride solution, extract the aqueous phase with 200 ml of dichloromethane and combine the organic layers. ...

Embodiment 2

[0028] Embodiment 2: contrast (original technology)

[0029] Add 10% sodium carbonate solution to the dichloromethane layer obtained in Implementation 1, adjust to PH9-10, separate the organic layer, wash with a small amount of purified water, combine the water layer, add 100ml of methanol, cool to -40°C, add 30% 110ml of sodium hydroxide, reacted at -30-35°C for 1 hour, added 100ml of 80% acetic acid to adjust the pH to 4-5, precipitated solid, continued to stir for 30 minutes, filtered, dried until the water content was less than 5‰, and obtained 3 -Hydroxymethyl cephalosporin 68g (compound (3)) content 99.2% (normalized method).

Embodiment 3

[0030] Embodiment 3. contrast (original technology)

[0031] Add 60g of compound (3) into 200ml tetrahydrofuran, stir to dissolve, cool to -60°C, add 50g isocyanate chlorosulfonate, react at -40-45°C for 1 hour, add 10% sodium chloride solution, hydrolyze 1 Hours, keep warm at 23-25°C, add diethyl hydrochloric acid dropwise to ph=1.3-1.5, precipitate solid particles, grow crystals for 30 minutes, cool to 5°C, filter after 30 minutes, and wash with DM. Dry until the water content is less than 3‰ to obtain 54 g of cefoxitin acid. Content: 99.3% (normalized method).

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Abstract

The invention relates to a method for preparing cefoxitin acid serving as the key raw material of cefoxitin sodium, and belongs to the field of chemical Chinese herbal medicines. In the method, 7-a-methoxyl cefalotin is subjected to deacetylation and carbamylation directly and simultaneously by isocyanide ester, and the processes of independent 3-position deacetylation and carbamylation are savedso as to obtain the cefoxitin acid directly. The cefoxitin sodium is obtained by the known method. A production process is simplified, the yield is high and the cost is low. In addition, the production link is reduced obviously and the cost is saved.

Description

Technical field: [0001] The invention belongs to the technical field of medicine, and relates to a preparation method of cefoxitin acid, a key intermediate of cefoxitin sodium. It avoids the original process of separately preparing 3-hydroxymethyl cephalosporin, and simplifies the production process. technical background: [0002] Cefoxitin (cefoxidin), chemical name: (6R, 7S)-3-carbamoyloxymethyl-7a-methoxy-8-oxo-7-[2-(2-thienyl)acetamido ]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid belongs to the second generation of highly effective, safe and broad-spectrum semi-synthetic antibiotics. The chemical structural formula is as follows (1): [0003] [0004] In the production process of producing cefoxitin both at home and abroad at present, all be starting raw material with cephalothin (sodium), and step is as follows: [0005] 1. 7a-Methoxidation: In the methanol / dichloromethane solvent system, sodium methoxide or lithium methoxide is added at ultra-low tempe...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D501/57C07D501/04
Inventor 白智全宁维松
Owner 重庆天地药业有限责任公司
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