Industrial preparation method of ertapenem

A technology of ertapenem and compounds, which is applied in the field of industrial preparation of ertapenem, can solve the problems of low total yield, high price, and low cost, and achieve the effect of simple operation process and high yield

Inactive Publication Date: 2012-02-15
湖南欧亚药业有限公司
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Problems solved by technology

[0019] Method 1 has many steps and the total yield is low; method 2, although in addition to the first step, the next few steps can be used to obtain the side chain of ertapenem in a 'one-pot method', but the relatively expensive diisopropyl phosphite is used and diphenylphosphorous oxychloride; method three is relatively low in cost compared to the first two methods, and is also more suitable for industrial production, but the protective group p-nitrobenzyloxycarbonyl used needs to be self-made, which increases the reaction steps

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  • Industrial preparation method of ertapenem
  • Industrial preparation method of ertapenem
  • Industrial preparation method of ertapenem

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Embodiment Construction

[0044] In order to make the technical means, creative features, work flow, and use methods of the present invention achieve the purpose and effect easily understood, the present invention will be further described below in conjunction with specific embodiments.

[0045] Synthesis of Compound II:

[0046]Add 131 grams of cis-4 hydroxy-L-proline (1.00 mol), 210 grams of sodium bicarbonate (2.50 mol) and 2000 ml of water into the reaction flask, and add 196 grams of chloroformic acid dissolved at 10-15 ° C dropwise under stirring Benzyl ester (1.15mol) in 400 ml of toluene solution, after the dropwise addition, return to room temperature and react for 20 hours. After the reaction, the reaction solution was separated, and the water layer was extracted twice with ether, each time using 300 ml, and the ether layer was discarded. , then add concentrated hydrochloric acid to the aqueous layer to adjust the pH=2, then extract twice with 800 ml and 600 ml of ethyl acetate, combine the e...

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Abstract

The invention discloses an industrial preparation method of ertapenem, comprising the following steps of: firstly synthesizing an ertapenem side chain (a compound V), and using the compound as a raw material together with 1beta-methyl vinyl phosphate (MAP) to prepare ertapenem. The invention has the following advantages of: the technology has fewer steps, the raw materials used are cheap and easily available, and the separation means is simple. Therefore, the preparation method is suitable for industrial production.

Description

technical field [0001] The invention relates to a novel preparation method of ertapenem. Background technique [0002] Ertapenem, chemical name (4R,5R,6S)-3-{(3S,5S)-5-[(3-carboxyphenyl)carbamoyl]-3-pyrrolidinyl}sulfur -6-(1-Hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid monosodium salt from Astra Zeneca and Merck The new broad-spectrum long-acting 1β-methyl carbapenem antibiotics jointly developed were launched in the United States and Europe in November 2001 and April 2002, respectively. This product has good antibacterial activity and pharmacokinetic properties, long half-life, and satisfactory results can be obtained by taking it once a day. It has been approved for the treatment of adults with complicated abdominal infection, community-acquired pneumonia, and complicated skin and soft tissue infection. , complicated urinary tract infections and gynecological infections, etc., and can be used for children over 3 months old. [0003] Ther...

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D477/20C07D477/06C07D207/16
Inventor 林开朝
Owner 湖南欧亚药业有限公司
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