A kind of preparation method of anti-infective cephalosporin

An anti-infection and head-like technology, applied in the direction of organic chemistry, can solve the problems of unfavorable preparation production, low product purity, and low total yield, so as to promote the acetalization reaction, shorten the reaction time, and have mild reaction conditions Effect

Active Publication Date: 2021-12-14
SHANDONG LUOXIN PHARMA GRP HENGXIN PHARMA CO LTD +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although this route avoids the use of chlorinated reagents that pollute the environment in conventional routes, the total yield is not high, and the product purity is not high, which is not conducive to the subsequent preparation production

Method used

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  • A kind of preparation method of anti-infective cephalosporin
  • A kind of preparation method of anti-infective cephalosporin
  • A kind of preparation method of anti-infective cephalosporin

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] 2-Oxoacetic acid hydrate (1.01g, 0.011mol, molecular weight 92.05) was dissolved in 10ml of dichloromethane, condensing agent CDI (2.59g, 0.016mol, molecular weight 162.15) was added in batches, TLC followed the reaction, and the reaction was completed Add the solution into the constant pressure funnel, add dropwise in the 40ml dichloromethane solution of compound II 7-MAC (5.25g, 0.01mol, molecular weight 524.61), the reaction temperature is 40°C, the reaction time is 10h, TLC traces the reaction is complete, wash the organic phase, dried over anhydrous sodium sulfate, filtered and concentrated to give compound III 5.73g (9.88x10 -3 mol, molecular weight 580.63), the yield is 98.8%, the HPLC purity is 99.6%, and the maximum is 0.02%.

Embodiment 2

[0029] 2-Oxoacetic acid hydrate (1.01g, 0.011mol, molecular weight 92.05) was dissolved in 10ml of dichloromethane, condensing agent DCC (3.3g, 0.016mol, molecular weight 206.33) was added in batches, TLC followed the reaction, and the reaction was completed Add the solution into the constant pressure funnel, add dropwise in the 40ml dichloromethane solution of compound II 7-MAC (5.25g, 0.01mol, molecular weight 524.61), the reaction temperature is 40°C, the reaction time is 10h, TLC traces the reaction is complete, wash the organic phase, dried over anhydrous sodium sulfate, filtered and concentrated to give compound III 5.71g (9.84x10 -3 mol, molecular weight 580.63), the yield is 98.4%, the HPLC purity is 99.5%, and the maximum is 0.02%.

Embodiment 3

[0031] 2-Oxoacetic acid hydrate (1.10g, 0.012mol, molecular weight 92.05) was dissolved in 10ml of dichloromethane, condensing agent CDI (3.24g, 0.02mol, molecular weight 162.15) was added in batches, TLC followed the reaction, and the reaction was completed Add the solution into the constant pressure funnel, add dropwise in the 40ml dichloromethane solution of compound II 7-MAC (5.25g, 0.01mol, molecular weight 524.61), the reaction temperature is 40°C, the reaction time is 10h, TLC traces the reaction is complete, wash the organic phase, dried over anhydrous sodium sulfate, filtered and concentrated to give compound III 5.72g (9.85x10 -3 mol, molecular weight 580.63), the yield is 98.5%, the HPLC purity is 99.7%, and the maximum is 0.03%.

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Abstract

The invention discloses a preparation method of an anti-infective cephalosporin drug. In the invention, compound III is prepared by reacting 7-MAC(II) with 2-oxoacetic acid hydrate, and compound III and 2-carbamoyl-3,3- Dimercaptoacrylic acid is subjected to acetalization reaction to prepare compound IV, and then cefotetan disodium (I) is obtained through deprotection and salt formation. The invention has simple synthesis route, mild reaction conditions, reduces the formation of impurities, improves the total yield and purity of products, and is suitable for industrial production.

Description

technical field [0001] The invention belongs to the technical field of drug synthesis, in particular to a preparation method of an anti-infective cephalosporin drug. Background technique [0002] Cefotetan disodium (cefotetan disodium), a β-lactam broad-spectrum antibiotic, is a dithiazol-methoxycephalosporin, which is stable to lactamase and has a strong binding to penicillin-binding protein, thereby blocking The synthesis of bacterial cell walls exerts strong bactericidal power in a short time, is extremely stable to the lactamase produced by various bacteria, and has a good antibacterial effect on Gram-negative bacteria and anaerobic bacteria. Clinically, it is mainly used for respiratory tract, lung infection, abdominal infection, urinary tract infection, gynecological infection and otitis media. It is used for intra-abdominal, skin and soft tissue infections, urinary tract, lower respiratory tract and obstetrics and gynecology infections caused by susceptible bacteria....

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D501/06C07D501/12C07D501/57
CPCC07D501/06C07D501/12C07D501/57
Inventor 刘晓彤李军军侯善波凌瑜莲管章委
Owner SHANDONG LUOXIN PHARMA GRP HENGXIN PHARMA CO LTD
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