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Synthesis method of panipenem and intermediates thereof

A synthesis method and compound technology, which are applied in the field of synthesis of panipenem and its intermediates, can solve the problems of great harm to the environment and operators, high price, and unsuitable for scale-up production.

Active Publication Date: 2013-05-15
湖南欧亚药业有限公司
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Problems solved by technology

[0020] Method 2 uses the dangerous azide reagent p-n-C 12 h 25 C 6 h 4 SO 2 N 3 , obviously not suitable for large-scale production, and expensive rhodium acetate is used; method 1 uses relatively safe iodobenzene acetate instead of the dangerous azide reagent p-n-C 12 h 25 C 6 h 4 SO 2 N 3 , but the synthesis of iodobenzene acetate needs to use a large amount of benzene, which is particularly harmful to the environment and operators; both methods use expensive tert-butyldimethylsilyl trifluoromethanesulfonate, which makes the whole process cost relatively high

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  • Synthesis method of panipenem and intermediates thereof
  • Synthesis method of panipenem and intermediates thereof
  • Synthesis method of panipenem and intermediates thereof

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[0056] 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.

[0057] Synthesis of Compound II:

[0058] Add 232 grams (2.00mol) of methyl acetoacetate, 237.6 grams (2.20mol) of benzyl alcohol and 3000 milliliters of toluene into the reaction flask, and slowly add 45 grams (0.30mol) of boron trifluoride ether solution with a concentration of 46% under stirring. ), reflux reaction for 6 hours, after the reaction, the reaction solution was poured into ice water, washed with saturated aqueous sodium bicarbonate solution until neutral, the water layer was extracted with 1 liter of toluene, the toluene layers were combined, washed with water, anhydrous sodium sulfate Dry; filter, the filtrate is concentrated to dryness, and the residue is distilled off under reduced pressure to remove...

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Abstract

The invention discloses a synthesis method of panipenem and intermediates thereof. The synthesis method comprises the following steps of: synthesizing intermediates 4R-[4a,5b,6b(R)]-carbonyl-6-(1-hydroxyethyl)-7-oxo-1-aza bicyclo[3.2.0] hept-2-ene-2-benzyl carboxylate (compound VII) and N-benzyl formate-3-(S)-3-mercaptopyrrolidine (compound VIII); and activating methylene with an iodization method to finally synthesize panipenem. In the method, high-danger azide or high-cost diphenyl iodoacetic acid is not used, and benzyl alcohol and benzyl chloroformate are used for replacing p-nitro benzylalcohol and p-nitro benzyl chloroformate used in the traditional process, thus the synthesis method has good reaction effect and low cost.

Description

technical field [0001] The invention relates to the field of synthesis of carbapenem antibiotics, in particular to a synthesis method of panipenem and an intermediate thereof. Background technique [0002] Panipenem (Panipenem), the chemical name is (5R,6S)-2-[(3S)-1-acetyliminopyrrolidin-3-yl]thio-6-[(1R)-1-hydroxyethyl Base]-2-carbapenem-3-carboxylic acid is a carbapenem antibiotic drug developed by Japan Sankyo Company, which was first listed in Japan in 1993. Clinically used in combination with the organic cation transport system inhibitor betamipron, it has strong antibacterial activity against Gram-positive bacteria, negative bacteria, aerobic bacteria and anaerobic bacteria, and the incidence of adverse reactions is low. Collectively well tolerated. It is clinically used for sepsis, osteomyelitis, lung infection, empyema, biliary tract infection, abdominal infection, meningitis, etc. caused by sensitive bacteria. The effective rate of penicillins, cephalosporins, a...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D477/20C07D477/06C07D207/12
Inventor 林开朝
Owner 湖南欧亚药业有限公司
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