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Crystalline cefuroxime axetil preparation method

A technology for cefuroxime axetil and cefuroxime axetil is applied in the field of chemical synthesis of cefuroxime axetil, can solve the problems of many impurities, safety risks, low boiling point of acetaldehyde, etc., achieves improved catalytic efficiency, improved product quality, simplified effect of preparation

Inactive Publication Date: 2018-09-28
BENGBU BBCA MEDICINE SCI DEV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] In the preparation method of cefuroxime axetil, copper chloride is mostly used as catalyst to prepare cefuroxime axetil, and the usage amount of copper chloride is relatively large, and copper chloride has certain toxicity, and copper ion is difficult to completely remove in the product, causes The appearance of the product is poor in color
[0004] In addition, in the prior art, the intermediate product 1-bromoethyl acetate of cefuroxime axetil uses acetaldehyde and acetyl bromide as raw materials, but the boiling point of acetaldehyde is low, the preparation process is not easy to operate, and its The catalyst with a naphthalene ring structure is a substance with a genotoxicity warning structure, and its safety has a greater risk
In addition, in the preparation process, dichloromethane needs to be used as the extractant, and dichloromethane needs to be recovered by distillation under reduced pressure at a certain temperature, and 1-bromoethyl acetate is extremely unstable above 10°C, so the above method The content of prepared 1-bromoethyl acetate is low, and there are many impurities, which bring adverse effects on the preparation of cefuroxime axetil

Method used

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Examples

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Embodiment 1

[0049] The present embodiment provides a kind of method for preparing 1-bromoethyl acetate, and described method is specifically:

[0050] In the reaction vessel, add 750.65mmol of acetyl bromide and 0.377mmol of zinc chloride, control the temperature at -5°C to 5°C, dropwise add 238.35mmol of paraldehyde, and maintain the above temperature for 5 hours to obtain crude 1-bromo Ethyl acetate; at a temperature of 0-5°C, wash the crude 1-bromoethyl acetate twice with 1500 mL of purified water, then dry it with 20 g of anhydrous sodium sulfate for 0.5 h, and filter it. That is, 1-bromoethyl acetate.

[0051] The total amount of 1-bromoethyl acetate obtained in this example is 95.6g, the yield: 80.06%, and the GC normalized purity: 97.34%.

Embodiment 2

[0053] The present embodiment provides a kind of method for preparing 1-bromoethyl acetate, and the difference between described method and embodiment 1 is:

[0054] At a temperature of 6-8°C, the crude 1-bromoethyl acetate was washed twice with 1500 mL of purified water, dried with 20 g of anhydrous sodium sulfate for 1 hour, and filtered to obtain 1-bromoethyl acetate ester;

[0055] The total amount of 1-bromoethyl acetate obtained in this example was 94.3g, the yield: 78.97%, and the GC normalized purity: 96.91%.

Embodiment 3

[0057] This embodiment provides a method for preparing cefuroxime axetil using 1-bromoethyl acetate prepared in Example 1, the method being specifically:

[0058] After mixing 400mL of dimethylacetamide and 100mL of purified water, add 0.283mol of cefuroxime acid and 0.192mol of potassium carbonate to it, stir evenly, adjust the temperature to -5°C to 0°C, and then slowly add 0.467mol to it for implementation The 1-bromoethyl acetate obtained in Example 1 was reacted while maintaining the above temperature, and the reaction endpoint was monitored by sampling. When the normalized purity of cefuroxime acid was less than or equal to 2%, it was the reaction endpoint (reaction time was about 1.5h).

[0059] Add 1000mL of ethyl acetate to the reaction solution after the reaction, use saturated sodium bicarbonate solution to adjust its pH value to 7-8, stir it at a speed of 90-150rpm for 1h, and then let it stand for stratification; After washing the organic layer with 500ml of 4% hy...

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Abstract

The invention relates to a crystalline cefuroxime axetil preparation method, which comprises: 1) carrying out a reaction on paraldehyde and acetyl bromide at a temperature of -10-10 DEG C under the action of a catalyst to obtain 1-bromoethyl acetate; 2) adding cefuroxime acid and a catalyst to the mixed solution of an organic solvent and water, adjusting the temperature to -20-5 DEG C, adding the1-bromoethyl acetate prepared in the step 1) to the mixed solution in a dropwise manner to obtain the crystalline cefuroxime axetil. According to the present invention, the method improves the traditional process, simplifies the process, improves the product quality, does not use the extraction solvent dichloromethane, greatly reduce the production cost, and improves the reaction efficiency and the purity of the final product.

Description

technical field [0001] The invention belongs to the technical fields of medicinal chemistry and pharmaceutical engineering, and in particular relates to a chemical synthesis method of cefuroxime axetil. Background technique [0002] Cefuroxime axetil was developed and marketed by the British Glaxo Company. It belongs to the second-generation cephalosporin. It has the characteristics of strong effect and wide antibacterial effect. Adverse reactions rarely occur in the drug, and it is widely used at home and abroad. The antibacterial activity of cefuroxime axetil is very low. After 3 to 4 minutes of oral absorption, it is rapidly hydrolyzed by non-specific esterase in the intestinal mucosa and portal circulation, releasing cefuroxime to exert its antibacterial effect. The antibacterial spectrum and antibacterial activity are the same as cefuroxime. Clinically, it is mainly used for mild and moderate respiratory tract infection, genitourinary system infection, skin and soft t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D501/34C07D501/04C07D501/12
Inventor 李立标郑爱陈昀林文龙徐新
Owner BENGBU BBCA MEDICINE SCI DEV
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