Preparation method of 7-aminocephalo-5-mercapto-1-methyltetrazole

A technology for tetrazolium and amino cephalosporins is applied in the field of preparation of cephalosporin intermediates 7-aminocephedrine tetrazolium, and can solve the problems of low content, poor quality, poor stability and the like

Inactive Publication Date: 2010-07-28
徐斌
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0008] The purpose of this invention is to provide a kind of production technique that can make high-purity 7-aminocephmetethrazol, to solve the poor quality of cephalosporin products such as cefmenoxime, cefpiramide etc. with this intermediate as mother nucleus , poor stability, high impurities such as related substances and polymers, and low content, etc., help to improve product quality and product stability, and better ensure the safety of clinical medication

Method used

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  • Preparation method of 7-aminocephalo-5-mercapto-1-methyltetrazole

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Embodiment 1

[0014] In a dry reaction flask, add 272g (1.0mol) of 7-ACA, 140g (1.2mol) of 5-mercapto-1-methyltetrazole and 1500ml of acetonitrile, cool to 0°C, add 1200ml of boron trifluoride-acetonitrile solution, Raise the temperature to 25°C, stir for 3 hours, and cool to 0°C in an ice bath. Under stirring, pour the reaction solution into 2000ml of 0.25% sodium bisulfite solution containing 0.5g EDTA pre-cooled to 0°C, adjust the pH of the solution to 2.5 with ammonia water at 0-2°C, continue stirring for 1h, filter, and filter cake Wash with acetonitrile, 30ml of water and acetone, and dry under vacuum below 40°C to obtain 298g of white powder with a weight yield of 110% and a melting point of 263-265°C.

Embodiment 2

[0016] In a dry reaction bottle, add 7-ACA 272g (1.0mol), 5-mercapto-1-methyltetrazole 140g (1.2mol) and acetonitrile 1500ml, cool to 5°C, add boron trifluoride-acetonitrile solution 1200ml, Raise the temperature to 25°C, stir for 3 hours, and cool to 5°C in an ice bath. Under stirring, pour the reaction solution into 2000ml of 0.25% sodium bisulfite solution containing 0.5g EDTA pre-cooled to 5°C, adjust the pH of the solution to 2.5 with ammonia water at 0-2°C, continue stirring for 1h, filter, and filter cake Wash with acetonitrile, 30ml of water and acetone, and dry under vacuum at below 40°C to obtain 305g of white powder with a weight yield of 112% and a melting point of 263-265°C.

Embodiment 3

[0018] In a dry reaction bottle, add 7-ACA 272g (1.0mol), 5-mercapto-1-methyltetrazole 140g (1.2mol) and acetonitrile 1500ml, cool to 5°C, add boron trifluoride-acetonitrile solution 1200ml, Raise the temperature to 30°C, stir for 3 hours, and cool to 0°C in an ice bath. Under stirring, pour the reaction solution into 2000ml of 0.25% sodium bisulfite solution containing 0.5g EDTA pre-cooled to 0°C, adjust the pH of the solution to 2.5 with ammonia water at 0-2°C, continue stirring for 1h, filter, and filter cake Wash with acetonitrile, 30ml of water and acetone, and dry under vacuum at below 40°C to obtain 302g of white powder with a weight yield of 111% and a melting point of 263-265°C.

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Abstract

The invention provides a preparation method of 7-aminocephalo-5-mercapto-1-methyltetrazole which is a cephems intermediate. In the method, 7-ACA is taken as the raw material; a suitable catalyst is added to a proper solvent to react with 5-mercapto-1-methyltetrazole to obtain the intermediate of 7-aminocephalo-5-mercapto-1-methyltetrazole. The intermediate is applied to the synthesis of cefmenoxime, cefpiramide and the like.

Description

technical field [0001] The invention relates to a method for preparing a cephalosporin intermediate, 7-aminocephmetethrazol, which is used in the synthesis of cefmenoxime, cefpiramide, etc., and belongs to the technical field of medicine and chemical industry. Background technique [0002] 7-Aminocephine-4-carboxylate, chemical name: 7-amino-3-[1-methyl-1H-tetrazole-5-thiomethyl]-ceph-3-ene-4-carboxylic acid. [0003] Chemical Structure: [0004] [0005] 7-aminocephmetetrazolium is used in the synthesis of cephalosporin products such as cefmenoxime and cefpiramide, etc. It is prepared by reacting 7-ACA with 5-mercapto-1-methyltetrazole. [0006] We have prepared cefmenoxime hydrochloride by using 7-aminocephmetetrazolium produced by different processes as raw materials. Through quality research and stability inspection, we found that the prepared product has poor stability, high impurity content, and easy to produce polymers. polymer impurities. A large number of clin...

Claims

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Application Information

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IPC IPC(8): C07D501/18C07D501/04
Inventor 徐斌
Owner 徐斌
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