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Preparation method of cefprozil

A technology of cefprozil and hydrate, which is applied in the field of synthesis of the second-generation cephalosporin antibiotic cefprozil, can solve the problems of low conversion rate, low product purity, and high content of trans isomers, and achieve low product loss , simple purification process and high yield

Active Publication Date: 2012-12-26
国药集团致君(苏州)制药有限公司
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Problems solved by technology

[0008] At present, the common shortcomings of the synthetic methods of cefprozil at home and abroad are that the reaction steps are too complicated, the conversion rate is low, and the product purity obtained is not high, and the trans isomer content is too high

Method used

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  • Preparation method of cefprozil
  • Preparation method of cefprozil
  • Preparation method of cefprozil

Examples

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Embodiment 1

[0053] (1) Under nitrogen protection, GCLE50g, NaI15g, Ph 3 P30g was added into chloroform, and the reaction was stirred at 10°C. The end point of the reaction is monitored by the liquid phase. After the reaction is completed, the organic phase is obtained by washing with water and standing for separation. The organic phase was cooled to -5°C, and sodium hydroxide was added to react for 100 min, and the end point of the reaction was monitored by TCL. After the reaction was completed, the organic phase was obtained by standing and layering. The temperature of the organic phase was lowered to -10° C., and isopropanol and acetaldehyde were added to react for 18 h. After the reaction was completed, the organic phase was obtained by standing and separating. After the organic phase was washed with water, it was concentrated under reduced pressure until crystallization appeared, and 30 ml of isopropanol was added to stir, and the temperature was lowered to 0° C., filtered, and drie...

Embodiment 2

[0057] (1) Under nitrogen protection, GCLE50g, NaI16g, Ph 3 P30g was added into dichloromethane, and the reaction was stirred at 15°C. The end point of the reaction is monitored by the liquid phase. After the reaction is completed, the organic phase is obtained by washing with water and standing for separation. The organic phase was cooled to 0°C, and sodium hydroxide was added to react for 80 min, and the end point of the reaction was monitored by TCL. After the reaction was completed, the mixture was left to stand and separated to obtain an organic phase. The temperature of the organic phase was lowered to -15°C, and isopropanol and acetaldehyde were added to react for 16 hours. After the reaction was completed, 200 ml of 20% sodium thiosulfate solution was added, stirred, and left to stand for stratification to obtain an organic phase. After the organic phase was washed with water, it was concentrated under reduced pressure until crystallization appeared, and 30 ml of iso...

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Abstract

The invention discloses a method for preparing and purifying cefprozil or a hydrate thereof. In the method, 4-methoxybenzyl 3-chloromethyl-7-(2-phenylacetamido)-3-cephem-4-carboxylate (GCLE) used as the raw material is processed by multistep reactions and purified to obtain the cefprozil. The preparation method has the advantages of simple process, high conversion rate and high cis-isomer content in cefprozil, and is suitable for synthetic techniques for large-scale industrial production. The yield of the cefprozil hydrate is higher than 85%, and the content of cis-isomer is up to 93%.

Description

technical field [0001] The invention relates to a method for synthesizing the second-generation cephalosporin antibiotic cefprozil, belonging to the field of pharmaceutical antibiotics. Background technique [0002] Cefprozil (Cefprozil), chemical name (6R, 7R)-7-[[(2R)-2-amino-2-(4-hydroxyphenyl) acetyl]amino]-8-oxo-3-[(E )-prop-1-enyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, its structural formula is shown in formula (I). [0003] [0004] Cefprozil is a second-generation cephalosporin antibiotic with a broad-spectrum antibacterial effect. Blood bacteria etc. also have inhibitory effect. The bactericidal mechanism is to hinder the synthesis of bacterial cell walls, which is safe and has extremely low adverse reactions. Cefprozil has been recorded in the United States Pharmacopoeia and is one of the varieties recommended by American clinicians. It is clinically used for mild to moderate skin infections and respiratory tract infections caused by sensitiv...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D501/22C07D501/06C12P35/04
Inventor 史利军孙元强
Owner 国药集团致君(苏州)制药有限公司
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