Method for preparing cephalosporin propylene

A technology of cefprozil and acetone, which is applied in the field of preparation of antibiotic drugs, can solve problems such as unstable quality, hard to find raw materials, and low yield, and achieve the effects of high yield, low cost, and reduced loss
CN101225088BInactive Publication Date: 2013-05-08南通康鑫药业有限公司
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Patent Information

Authority / Receiving Office
CN · China
Patent Type
Patents(China)
Current Assignee / Owner
南通康鑫药业有限公司
Publication Date
2013-05-08
Estimated Expiration
Not applicable · inactive patent

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Abstract

The invention discloses a preparation method of cefprozil, which comprises: 7-amin cethalosporanic acid (7-ACA) reacts with triphenyl phosphine to get 7- trimethylsilyl amino-3-triphenyl phosphate methylene-4-cethalosporanic acid trimethylsilyl ester through silanization protection and iodination reagent replacing under the condition of catalyst existing; WITTIG reaction is made for the product and acetaldehyde to get 7-trimethylsilyl amino -3-(propenyl-1-alkenyl)-4-cethalosporanic acidtrimethylsilyl ester; then the compound reacts with D-para hydroxybenzene glycine dane potassium salt to geta compound (6R, 7R)-7-[(2R)-2- ethoxycarbonyl-1-methyl - ethylene amino (4-trimethylsilyl oxyphenyl) acetamido group(amide)]-8-oxo-3- (1- propenyl)-5-thio-1- heterobicycle [4.2.0] octylene-2-ene-2-carboxylic acid trimethylsilyl ester; hydrolytic treatment is then used to get the cefprozil. The invent adopts the method of one pot and can participate in next reaction without separating intermediateproducts. The preparation method of cefprozil has the advantages of low cost, convenient operation and high overall yield, adapting to demands of industrial production.
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Description

Technical field

[0001] The invention relates to a preparation method of an antibiotic drug, in particular to a process for synthesizing the antibiotic drug cefprozil with 7-ACA (7-aminocephalosporanic acid) as a starting material.

[0002] Background technique

[0003] Cefprozil (cefprozil), chemical name (6R, 7R)-7-[(2R)-amino(4-hydroxyphenyl)acetamido]-8-oxo-3-(1-propenyl)-5 -Thio-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, as a monohydrate for medicinal purposes, is a broad-spectrum cephalosporin antibiotic developed by Bristol-Myers Squibb , For G + , G - The antibacterial activity of bacteria and anaerobic bacteria is very strong, and the G + Bacterial activity is particularly outstanding.

[0004] At present, the reported methods for synthesizing cefprozil basically adopt GCLE and GCLH routes, such as US Patent US4694079, Chinese Patent Publication No. CN101024649, "Synthesis of Cefprozil"-Chinese Journal of Pharmaceutical Industry. 2004, 35(7): 388, etc. . The main ro...

Claims

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