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Method for preparing cephalonium from 7-aminocephalosporanic acid at one step

A technology of aminocephalosporanic acid and ceftaroning, which is applied in the field of preparation of ceftaroning, can solve the problems of restricting the industrial production of ceftaroning, difficulty in obtaining, and high price, etc., and achieves improved production efficiency, simple operation, and low market price Effect

Active Publication Date: 2014-05-07
FUJIAN FUKANG PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the preparation process of cefuroxime provided by this invention patent is simple and easy to operate, the yield is low, and the highest is no more than 45%.
At the same time, since the patent uses 1-((7-amino-2-carboxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl)methyl base)-4-carbamoylpyridine hydrochloride (abbreviated as 7-IACA) as the raw material, which is expensive and difficult to obtain, which greatly limits the industrial production of ceftaroline

Method used

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preparation example Construction

[0024] The invention discloses a preparation method for preparing cefuronan from 7-aminocephalosporanic acid in one step. The preparation method comprises the following steps: 1) adding 7-aminocephalosporanic acid to water at 0-10°C; the 7-aminocephalosporanic acid - The mass ratio of aminocephalosporanic acid to water is 1:2-20;

[0025] 2) Use lye to adjust the pH value of the solution in step 1) to 5.0-8.5;

[0026] 3) First add organic solvent to the solution obtained in step 2), then add thiopheneacetyl chloride and ethyl acetate, stir and react at 0-10°C for 1-3 hours, add lye dropwise during the reaction to maintain the pH value of the solution 6.0-8.0; the mass ratio of the 7-aminocephalosporanic acid, organic solvent, thiopheneacetyl chloride and ethyl acetate is 1:2-8:0.6-1.5:10-25;

[0027] 4) After the reaction is over, let stand and separate layers, add ethyl acetate to the water phase for extraction and washing for 2-3 times, then transfer the water phase to the...

Embodiment 1

[0033] A preparation method for preparing cefuroxime by one-step method of 7-aminocephalosporanic acid, which comprises the following steps: 1) adding 7-aminocephalosporanic acid to water at 0-5°C; said 7-aminocephalosporanic acid and The mass ratio of water is 1:2;

[0034] 2) Adjust the pH value of the solution in step 1) to 5.0 with triethylamine solution;

[0035] 3) First add acetone to the solution obtained in step 2), then add thiopheneacetyl chloride and ethyl acetate, stir and react at 0-5°C for 3 hours, add triethylamine solution dropwise during the reaction to maintain the pH of the solution 6.0; the mass ratio of the 7-aminocephalosporanic acid, acetone, thiopheneacetyl chloride and ethyl acetate is 1:8:1.0:10;

[0036] 4) After the reaction is over, let it stand still, separate layers, add ethyl acetate to the water phase for extraction and washing twice, and then transfer the water phase to the carbon removal tank;

[0037] 5) Add activated carbon to the water ...

Embodiment 2

[0042] A preparation method for preparing cefuronan by one-step method of 7-aminocephalosporanic acid, which comprises the following steps: 1) adding 7-aminocephalosporanic acid to water at 5-10°C; the 7-aminocephalosporanic acid and The mass ratio of water is 1: 20;

[0043] 2) Adjust the pH value of the solution in step 1) to 8.5 with aqueous sodium hydroxide solution;

[0044] 3) First add methanol to the solution obtained in step 2), then add thiopheneacetyl chloride and ethyl acetate, stir and react at 5-10°C for 1 hour, add aqueous sodium bicarbonate solution dropwise during the reaction to maintain the pH of the solution 8.0; the mass ratio of the 7-aminocephalosporanic acid, methanol, thiopheneacetyl chloride and ethyl acetate is 1:2:0.6:25;

[0045] 4) After the reaction is over, let stand, separate layers, add ethyl acetate to the water phase for extraction and washing for 3 times, then transfer the water phase to the carbon removal tank;

[0046] 5) Add activated ...

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Abstract

The invention discloses a method for preparing cephalonium from 7-aminocephalosporanic acid at one step. The method comprises the following steps: (1) adding 7-aminocephalosporanic acid into water with the temperature of 0-10 DEG C; (2) regulating the pH value of the solution; (3) adding an organic solvent, tiophencacetyl chloride and ethyl acetate, and reacting for 1-3h while stirring at the temperature of 0-10 DEG C; (4) after the reaction is ended, standing for layering; (5) adding activated carbon into a water phase for decoloring, and carrying out suction filtration; (6) adjusting the pH value of the filtrate, then, adding isonicotinamide, and reacting at the temperature of 15-50 DEG C; (7) after the reaction is ended, growing the grain for over 1h; (8) filtering to obtain a crystal, and drying to obtain the cephalonium. The cephalonium is prepared at one step, and an intermediate is not needed to be separated and extracted in the reaction process, so that the method is simple and convenient in operation, simple in reaction step and high in yield; the 7-aminocephalosporanic acid is used as the raw material and is simple and easy to obtain and low in market price, so that the production cost is greatly reduced.

Description

technical field [0001] The invention relates to a preparation method of cefaroning, in particular to a preparation method of cefaroning by one-step method of 7-aminocephalosporanic acid. Background technique [0002] Ceftaroline, Chinese alias (6R,7R)-3-[(4-formamido-1-pyridine) methyl]-8-oxo-7-[(2-thiophen-2-ylacetyl)amino] -5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid inner salt. It is mainly used for the prevention and treatment of mastitis in the dry period of dairy cows. The drug belongs to long-acting broad-spectrum antibiotics, which can effectively treat and prevent various bacterial infections of dairy cows during the dry period. [0003] The patent number is 201310189258.6, and the invention patent titled "Preparation Method of Cefuroxime" discloses a method for the preparation of Cefuroxime. The patent uses 7-ICAC and thiophene acetyl chloride as raw materials, at a pH of 6- The product was obtained after 7 reactions. Although the preparation technolo...

Claims

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Application Information

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IPC IPC(8): C07D501/56C07D501/04C07D501/06
CPCC07D501/04C07D501/06C07D501/46
Inventor 姚志扬
Owner FUJIAN FUKANG PHARMA
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