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Preparation method of cefbuperazone side chain

A technology of cefbuperazone and side chains, applied in the field of preparation of cefbuperazone side chains, can solve the problems of large amount of solvent used, complex process operation, high reaction cost, etc.

Inactive Publication Date: 2012-12-26
HARBIN PHARMA GRP CO LTD GENERAL PHARMA FACTORY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005]Cefbuperazone side chain is synthesized from two raw materials D-threonine and DEPT, domestic abstract "Cefbuperazone Synthesis", Journal of Chengdu University, No. 28 Volume No. 3, 199-201, these two raw materials are selected as starting materials, but the post-reaction treatment process needs to be concentrated, the amount of solvent used makes the reaction cost high, and the process operation is complicated. The present invention aims at the above shortcomings and improves the side chain Synthesis process, using isoelectric point for crystallization, the side chain yield is greatly improved

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  • Preparation method of cefbuperazone side chain

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Embodiment 1

[0039] Synthesis of side chains:

[0040] In a dry 250ml three-necked flask, add 7.4g of D-threonine and 80ml of anhydrous DCM, stir, and pass through the nitrogen replacement system. Add 10 ml of trimethylchlorosilane dropwise at room temperature, cool down to 0°C in an ice bath, slowly add 12 ml of triethylamine dropwise, control the dropping temperature at 0°C, and naturally warm up to room temperature after dropping, and react for 2 hours. After the reaction was completed, the temperature was cooled to 0°C in an ice bath, and 20ml of anhydrous DCM solution of 12g of EDPC was added dropwise at a temperature of 5°C.

[0041] Post-reaction treatment: suction filtration, washing the filter cake with DCM. The filtrate was washed with 20ml of water for 30min and separated. The organic phase was adjusted to pH 8.0 with saturated sodium carbonate solution. Separate the liquids, wash the organic phase twice with 40ml saturated sodium bicarbonate solution, 5min each time, and co...

Embodiment 2

[0043] Synthesis of side chains

[0044] In a dry 250ml three-necked flask, add 15g of D-threonine and 162ml of anhydrous DCM, stir, and pass through the nitrogen replacement system. Add 20 ml of trimethylchlorosilane dropwise at room temperature, cool down to 5°C in an ice bath, slowly add 24 ml of triethylamine dropwise, and control the dropwise temperature at 10°C, then naturally warm up to room temperature after dropping, and react for 2 hours. After the reaction was completed, the temperature was cooled to 0°C in an ice bath, and 40ml of anhydrous DCM solution of 24.3g of EDPC was added dropwise at a temperature of 10°C.

[0045] Post-reaction treatment: suction filtration, washing the filter cake with DCM. The filtrate was washed with 40ml of water for 30min and separated. The organic phase was adjusted to pH 7.0 with saturated sodium carbonate solution. Separate the liquids, wash the organic phase with 80ml of saturated sodium bicarbonate solution twice for 5min ea...

Embodiment 3

[0047] Synthesis of side chains

[0048] In a dry 250ml three-necked flask, add 20g of D-threonine and 216ml of anhydrous DCM, stir, and pass through the nitrogen replacement system. Add 27 ml of trimethylchlorosilane dropwise at room temperature, cool down to 2°C in an ice bath, slowly add 32.4 ml of triethylamine dropwise, and control the dropping temperature at 5°C, then naturally warm up to room temperature after dropping, and react for 2 hours. After the reaction was completed, the temperature was cooled to 0°C in an ice bath, and 54ml of anhydrous DCM solution of 32.4g of EDPC was added dropwise at a temperature of 6°C.

[0049]Post-reaction treatment: suction filtration, washing the filter cake with DCM. The filtrate was washed with 54ml of water for 30min and separated. The organic phase was adjusted to pH 10.0 with saturated sodium carbonate solution. Separate the liquids, wash the organic phase with 108ml of saturated sodium bicarbonate solution twice for 5min...

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Abstract

The invention relates to a preparation method of a cefbuperazone side chain; and the cefbuperazone side chain is obtained by synthesizing two raw materials of D-threonine and DEPT through two-step reaction. According to the invention, reaction steps comprise cefbuperazone side chain synthesis and reaction liquid after treatment. According to the invention, in the after treatment process, crystallization of an extracting liquor uses a pH value controlling crystallization method, so that a concentrating link is omitted; and the invention is to provide a cefbuperazone immediate, which is prepared by simple technical steps and is suitable for industrial production.

Description

technical field [0001] The present invention relates to a kind of preparation method of cefbuperazone side chain, particularly a kind of preparation method of cefbuperazone intermediate. Background technique [0002] Cefbuperazone is a derivative of cephamycin, and its effect is similar to that of cefmetazole. It has good antibacterial effect on Gram-negative bacteria and anaerobic bacteria. Cefbuperazone is a third-generation cephalosporin antibiotic developed by Japan Toyama Chemical Industry Pharmaceutical Co., Ltd. in the 1970s and launched in 1985. Cefbuperazone has a similar mechanism of action as other cephalosporins, mainly by inhibiting bacterial cell walls Synthesis to play a bactericidal effect. Cefrazone is a broad-spectrum antibacterial drug against G + , G - Both bacteria and anaerobic bacteria have effects, and the effect on anaerobic bacteria is better than that of general third-generation cephalosporins. Cephbuperazone increases enzyme resistance and sta...

Claims

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Application Information

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IPC IPC(8): C07D241/08
Inventor 孙志嘉杨新春成佳兴
Owner HARBIN PHARMA GRP CO LTD GENERAL PHARMA FACTORY
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