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Preparation method of cephalosporin antibiotic parent nucleus GCLE (7-phenylacetamido-3-cephem-4-carboxylic p-methoxybenzyl ester)

A cephalosporin and antibiotic technology is applied in the field of preparation of new cephalosporin antibiotic parent nucleus GCLE, which can solve problems such as excess industrial salt of penicillin, and achieve the effects of good application and promotion significance, mild reaction conditions and easy operation.

Inactive Publication Date: 2013-01-09
广东省石油化工研究院
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  • Abstract
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  • Claims
  • Application Information

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Problems solved by technology

In this way, a pair of contradictions are formed: on the one hand, my country spends a large amount of foreign exchange every year to purchase GCLE or cephalosporin raw materials synthesized from it, and the raw material penicillin industrial salt for the production of this product is severely surplus in the domestic market

Method used

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  • Preparation method of cephalosporin antibiotic parent nucleus GCLE (7-phenylacetamido-3-cephem-4-carboxylic p-methoxybenzyl ester)
  • Preparation method of cephalosporin antibiotic parent nucleus GCLE (7-phenylacetamido-3-cephem-4-carboxylic p-methoxybenzyl ester)
  • Preparation method of cephalosporin antibiotic parent nucleus GCLE (7-phenylacetamido-3-cephem-4-carboxylic p-methoxybenzyl ester)

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Embodiment 1

[0044] The production process flow chart is attached figure 1 shown.

[0045] Step (1) Oxidation: Place a glass three-necked bottle containing 103.5 grams of 8.5% peracetic acid solution in a cold trap, cool down to -5°C, and start mechanical stirring; 37.2 grams (0.1mol) of penicillin G potassium salt (city purchased), slowly added to the three-necked bottle, and finished within 30 minutes. The reaction was continued for 2 hours. Stop the reaction, transfer the reaction solution to a 200 ml beaker, heat up to 30°C, and slowly add 3M H 2 SO 4 , adjust the pH value to 1.5, and after reaching the pH value of 1.5, place the beaker in ice water to cool for 60 minutes. Suction filtration, the filter cake was washed 5 times with deionized water (DI water) until no sulfate ions were detected, and the product was vacuum-dried at 60°C. A white powdery solid was obtained. The yield is 90%. The melting point of the product is measured with a B-type tube, and the melting point...

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Abstract

The invention discloses a preparation method of cephalosporin antibiotic parent nucleus GCLE (7-phenylacetamido-3-cephem-4-carboxylic p-methoxybenzyl ester), which comprises the following steps: oxidizing the raw material penicillin G potassium salt with peroxyacetic acid to obtain penicillin sulfoxide, reacting the penicillin sulfoxide with methoxybenzyl chloride to obtain penicillin sulfoxide ester, carrying out ring-opening reaction on the penicillin sulfoxide ester and a ring opening agent 2-mercaptobenzothiazole to prepare an intermediate azabutanone sulfinic acid under the protection of a protective agent; chlorinating the intermediate with a chlorinating agent, and cyclizing in a DMF (N,N-dimethylformamide) and nitrogenous environment to obtain the cephalosporin antibiotic parent nucleus GCLE. The invention optimizes the key technological conditions, fully utilizes the abundant penicillin industrial salt raw material resources in China, and successfully acquires a new technical scheme for preparing GCLE. The invention has the advantages of high safety, high efficiency, high yield and environmental protection, and provides important technical support for research and application of cephalosporin drugs.

Description

technical field [0001] The invention belongs to the technical field of synthesis of cephalosporin pharmaceutical intermediates, and in particular relates to a preparation method of a novel cephalosporin antibiotic mother nucleus GCLE. Background technique [0002] GCLE (7-Phenylacetamido-3-Chloromethyl Cesporenoic Acid p-Methoxybenzyl Ester) was developed by Japan in the 1990s, and it is another kind developed after 7-ACA and 7-ADCA. Novel cephalosporin antibiotic mother nucleus. GCLE (7-phenylacetamido-3-chloromethyl cespranenoic acid p-methoxybenzyl ester) can synthesize dozens of cephalosporin products, such as cefixime, cefdinir, cefotiam, cefazolin, cephalosporin Nixie, cefotaxime, ceftriaxone, cefodizime, ceftriaxone, cefoperazone, cefotaxime, ceftriaxone, cefsulfonyl, etc. Among the cephalosporin varieties prepared with 7-ACA as the mother nucleus, more than 60% of the varieties can be produced by GCLE, and when GCLE is used as the mother nucleus to produce cephalos...

Claims

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Application Information

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IPC IPC(8): C07D501/24C07D501/08
Inventor 叶瑾亮翁行尚张小春陈伟健
Owner 广东省石油化工研究院
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