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Preparation method of descarbamoyl cefuroxime

A technology of carbamoyl head and amino cephalosporanic acid is applied in the field of preparation of decarbamoyl cefuroxime, which can solve the problems of reducing chemical reaction process, harsh temperature conditions, shortening production cycle and the like, and achieves production equipment and operation protection. Low requirements, mild reaction conditions, and the effect of shortening the production cycle

Inactive Publication Date: 2013-12-18
GUANGDONG LIGUO PHARMACY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Disadvantages of the existing technology: the production process is complex and the production cycle is long; the temperature of the condensation reaction process is required to be controlled below -35°C, and the energy consumption is large; the process uses a highly toxic methanol solvent, which is not conducive to the protection of the operator and affects the production. High requirements for equipment and operation protection
Although this method allows the use of ethanol crystallization and reduces the toxicity of the raw materials used, the reaction is generally carried out at about -10°C or in an ice-water bath, resulting in high energy consumption, long production cycle, and harsh operating conditions.
[0005] Chinese patent application CN101289457A discloses that D-7-ACA is used to replace 7-ACA as a raw material to react with SMIA acid chloride to synthesize decarbamoyl cefuroxime. This process reduces the chemical reaction process required in the synthesis and shortens the production cycle, but The temperature conditions are still very harsh, the reaction temperature is generally between -60~-40°C, and the product yield is not high, the molar yield is only 90.6%

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Add 150mL of purified water and 37.5g of deacetyl-7-aminocephalosporanic acid (D-7-ACA) into the reaction flask, add sodium hydroxide solution under stirring, and cool down to 5°C until D-7 - ACA is completely dissolved;

[0032] Add 11.25g of phosphorus pentachloride to another reaction flask, and add 90mL of methylene chloride, add 22.5g of 2-methoxyimino-2-furan ammonium acetate (SMIA) under stirring, and control the temperature at 20°C. React for 0.5 hours, and the end point of the reaction is monitored by HPLC (SMIA residue ≤ 1%) to obtain the acid chloride solution;

[0033] Add the acid chloride solution to the D-7-ACA solution for condensation reaction, control the reaction temperature at about 15°C, and monitor the reaction end point by HPLC (D-7-ACA residue ≤ 1%),

[0034] After the condensation reaction is over, stand and separate to obtain the aqueous phase solution and add 18.75ml of ethanol, add hydrochloric acid solution dropwise to the aqueous phase sol...

Embodiment 2

[0036] Add 150mL of purified water and 42.9g of deacetyl-7-aminocephalosporanic acid (D-7-ACA) into the reaction flask, add sodium hydroxide solution under stirring, and cool down to 8°C until D-7 - ACA is completely dissolved;

[0037] Add 18g of phosphorus pentachloride to another reaction flask, and add 180mL of methylene chloride, add 30g of 2-methoxyimino-2-furan ammonium acetate (SMIA) under stirring, and control the temperature at 23°C for reaction 1 Hours, the end of the reaction was monitored by HPLC (SMIA residue ≤ 1%), and the acid chloride solution was obtained;

[0038] The acid chloride solution is added to the D-7-ACA solution for condensation reaction, the reaction temperature is controlled at about 18°C, and the reaction end point is monitored by HPLC (D-7-ACA residue ≤ 1%),

[0039] After the condensation reaction is over, stand and separate to obtain the aqueous phase solution and add 42.9ml of ethanol, add hydrochloric acid solution dropwise to the aqueous...

Embodiment 3

[0041] Add 150mL of purified water to the reaction flask, add 50g of deacetyl-7-aminocephalosporanic acid (D-7-ACA), add sodium hydroxide solution under stirring, and cool down to 10°C until D-7- ACA is completely dissolved;

[0042] Add 20g of phosphorus pentachloride to another reaction flask, and add 200mL of methylene chloride, add 35g of 2-methoxyimino-2-furan ammonium acetate (SMIA) under stirring, and control the temperature at 25°C for reaction 1 Hours, the end of the reaction was monitored by HPLC (SMIA residue ≤ 1%), and the acid chloride solution was obtained;

[0043] Add the acid chloride solution to the D-7-ACA solution for condensation reaction, control the reaction temperature at about 20°C, and monitor the reaction end point by HPLC (D-7-ACA residue ≤ 1%),

[0044] After the condensation reaction is over, stand and separate to obtain the aqueous phase solution and add 50ml of ethanol, add hydrochloric acid solution dropwise to the aqueous phase solution to cr...

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PUM

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Abstract

The invention discloses a preparation method of descarbamoyl cefuroxime, which comprises the following steps: performing condensation reaction on 3-deacetyl-7-aminocephalosporanic acid used as a parent nucleus for synthesis of the descarbamoyl cefuroxime and a 2-methoxyimino-2-furanammoniumacetate acyl chloride solution, standing, crystallizing with ethanol / hydrochloric acid, washing, performing vacuum filtration, and drying to obtain the product descarbamoyl cefuroxime. The method uses 3-deacetyl-7-aminocephalosporanic acid as the raw material, uses ethanol for crystallization, shortens the production cycle, and is safe and low in toxicity; and meanwhile, the method is mild in reaction conditions and convenient to realize industrial production.

Description

technical field [0001] The invention belongs to the field of preparation of pharmaceutical intermediates, in particular to a preparation method of decarbamoyl cefuroxime. Background technique [0002] Cefuroxime was produced in the United Kingdom. In 1975, Glaxo Company took the lead in developing the second-generation semi-synthetic cephalosporin, namely cefuroxime. Cefuroxime began to play an important role in clinical medicine. Cefuroxime is a broad-spectrum antibiotic, targeting Gram-negative bacteria and Gram-positive bacteria. Cefuroxime inhibits the bacterial cell wall of the patient, making it difficult to synthesize, or causing damage and defects in the bacterial cell wall of the patient, resulting in the death of the bacteria , so as to achieve the purpose of antibacterial. At present, cefuroxime is widely used in clinical medicine, and it can be used in the treatment of infection or postoperative infection of various diseases such as genitourinary system, bones, ...

Claims

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Application Information

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IPC IPC(8): C07D501/34C07D501/06
Inventor 许伟龙
Owner GUANGDONG LIGUO PHARMACY
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