Method for preparing cefprozil mother nucleus 7-amino-3-acryl cephalosporanic acid

A technology of propenyl cephalosporanic acid and cefprozil parent nucleus, applied in the direction of organic chemistry, etc., can solve the problems of low purity of cefprozil parent nucleus, low yield, incomplete decolorization and the like

Active Publication Date: 2015-10-28
HEBEI JIUTIAN BIOLOGICAL PROD CO LTD
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Problems solved by technology

[0013] In order to solve the problems of low purity, incomplete decolorization and low yield of the cefprozil parent nucleus prepared in the prior art, the present inventio...

Method used

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  • Method for preparing cefprozil mother nucleus 7-amino-3-acryl cephalosporanic acid
  • Method for preparing cefprozil mother nucleus 7-amino-3-acryl cephalosporanic acid
  • Method for preparing cefprozil mother nucleus 7-amino-3-acryl cephalosporanic acid

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Experimental program
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Embodiment 1

[0037] Test equipment: dry 500ml four-neck flask, 50ml constant pressure dropping funnel, 500cm spherical condenser, constant temperature water bath, low temperature circulation pump, etc.

[0038] Detection instrument: Agilent liquid phase

[0039] Detection conditions and methods: C18 250mm×4.6um, detection wavelength 254nm (central control) 280 (product), flow rate 1.0ml / min

[0040] Mobile phase: 0.0115% ammonium dihydrogen phosphate solution: acetonitrile = 9:1

[0041] Add 45g of 7-ACA, 45.9g of triphenylphosphine, 225g of dichloromethane, and 0.045g of iodine into a 500ml four-neck flask in sequence, raise the temperature to 35°C, start to add 40g of hexamethyldisilazane dropwise, and finish dropping in 30 minutes , keep the reaction temperature below 40°C, after the dropwise addition, raise the temperature to 45°C and continue the reaction for 3 hours. ℃, take samples for 3 hours to detect that the residue of raw materials is ≤0.5%, cool down to -5℃, add DMF180g, N,O...

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Abstract

The invention relates to a method for preparing cefprozil mother nucleus 7-amino-3-acryl cephalosporanic acid. According to the method, 7-amino cephalosporanic acid is adopted as a starting raw material, silylation protection, phosphorusylide formation, wittig reaction and silylation protection group removing are sequentially performed to obtain a cefprozil mother nucleus crude product, and a cefprozil mother nucleus crude product refining post-treatment process is added, wherein the cefprozil mother nucleus crude product refining post-treatment process comprises: a, amine salt forming, b, decolorization treatment, and c, cefprozil mother nucleus refined product preparing. According to the present invention, the prepared cefprozil mother nucleus has characteristics of high purity, good crystalline form, good color and high yield, the ratio of the E isomer content to the Z type isomer content is optimal so as to ensure the improved quality of the cefprozil prepared at the latter stage, the cefprozil mother nucleus purity can achieve 99.7%, the 7-ADCA is less than or equal to 0.15%, the crystalline form is hexagonal columnar, separation is easy, the patina is not easily generated, the color is less than or equal to Y-4 and is basically bright white, the yield is high, the quality is good, and the mass yield is more than 65%.

Description

technical field [0001] The technical field of chemical synthesis of the present invention specifically relates to a method for preparing cefprozil core 7-amino-3-propenyl cephalosporanic acid. Background technique [0002] Cefprozil mother nucleus is the raw material that is used to prepare cefprozil, and the method for synthesizing cefprozil mother nucleus has three kinds at present: one, take 7-ACA as starting material to synthesize cefprozil mother nucleus; Two, take GCLE as starting material to synthesize cephalosporin Propylene mother nucleus; 3. Synthesis of cefprozil mother nucleus with GCLH as the starting material. [0003] 1. Taking 7-ACA as the starting material to synthesize the cefprozil core: first, in the presence of a solvent, 7-ACA is protected by silanization in the low temperature range, replaced by 7-ACA, and reacted with triphenylphosphine to obtain compound (3), Then react with acetaldehyde in the presence of an alkali metal salt to obtain compound (4)...

Claims

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Application Information

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IPC IPC(8): C07D501/22C07D501/04C07D501/12
CPCC07D501/04C07D501/12C07D501/22
Inventor 赵社彬陈波邓功燕
Owner HEBEI JIUTIAN BIOLOGICAL PROD CO LTD
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