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Preparation method of anti-form cefuroxime derivative

A technology for trans-cefturoxime derivatives, which is applied in the field of preparation of trans-cefturoxime derivatives, can solve the problems of high preparation cost and low yield, and achieve the effect of efficient preparation

Pending Publication Date: 2019-06-28
GUANGDONG LIGUO PHARMACY
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  • Claims
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Problems solved by technology

[0003] The purpose of the present invention is to provide a preparation method of trans cefuroxime derivatives to solve the problems of high preparation cost and low yield of cefuroxime trans impurities in the prior art

Method used

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  • Preparation method of anti-form cefuroxime derivative
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  • Preparation method of anti-form cefuroxime derivative

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preparation example Construction

[0019] The present invention relates to a kind of preparation method of trans cefuroxime derivatives, comprising:

[0020] A. Dissolve phosphorus pentachloride in a solvent, lower the temperature to -30-10°C, and add cis-methoxyiminofuran ammonium acetate (cis-SMIA ammonium salt, CAS registration number is 97148- 39-5), control -30~10℃ and stir for 60-240min, react to obtain cis-methoxyiminofuran acetyl chloride solution (cis-SMIA acid chloride solution); wherein, the solvent includes but not limited to esters, alcohols, hydrocarbons ketones, aldehydes, amines, nitriles, ethers, etc.; amide reagents include but not limited to N,N-dimethylformamide, N,N-dimethylacetamide, etc.; phosphorus pentachloride and The mass ratio of the solvent is 1:2 to 12, that is, 1:2 to 1:12, the mass ratio of phosphorus pentachloride to solvent is preferably 1:3 to 8; the mass ratio of amide reagent to phosphorus pentachloride is 0.2 to 3:1, that is, 0.2:1 to 3:1; the mass ratio of phosphorus pent...

Embodiment 1

[0047] Preparation of trans-methoxyimidofuranacetyl chloride: Add 35g of phosphorus pentachloride to 180g of ethyl acetate, mix well, cool down to 0-10°C, add 50g of dimethylacetamide, then add 30g of cis-methoxyimide Ammonium furanacetate ammonium salt, stirred at 0-10°C for 150 minutes to prepare cis-methoxyimidofuranacetyl chloride, added 16g of acetone, then added 3.8g of 10% sulfuric acid solution, and stirred at 50°C for 6 hours to obtain trans Methoxyiminofuranacetyl chloride, purity 96.3%.

Embodiment 2

[0049] Preparation of trans-methoxyimidofuranacetyl chloride: Add 35g of phosphorus pentachloride into 230g of dichloromethane, stir to dissolve, cool down to -5~0°C, add 40g of dimethylformamide, and then add 25g of cis-formaldehyde Oxyiminofuran acetic acid ammonium salt, controlled at -5~-5°C and stirred for 130 minutes to prepare cis-methoxyimidofuranacetyl chloride, added 10g of ethanol, then added 5g of 15% sodium hydroxide solution, controlled at 60°C and stirred for reaction After 4 hours, trans-methoxyimidofuranacetyl chloride was obtained with a purity of 96.9%.

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Abstract

The invention relates to a preparation method of an anti-form cefuroxime derivative. The preparation method comprises the steps that A, phosphorus pentachloride is dissolved in a solvent, in the presence of an acidamide reagent, cis-form methoxyiminofurylacetic acid amonium salt is added, and through a reaction, a cis-form methoxy-imino furan acetyl chloride solution is obtained; B, a solvent is added to the cis-form methoxy-imino furan acetyl chloride solution, then strong acid or strong base is added, stirring is conducted, and the cis-form methoxy-imino furan acetyl chloride solution is converted into anti-form methoxy-imino furan acetyl chloride. According to the preparation method of the anti-form cefuroxime derivative, on the basis of original preparation of the anti-form methoxy-imino furan acetyl chloride, an innovative method is provided, by adding a proper quantity of solvent, in the presence of the strong acid or strong base, cis-trans isomerism conversion is conducted, andaccordingly the high-purity anti-form cefuroxime derivative can be efficiently prepared through a synthesis method.

Description

technical field [0001] The invention relates to the technical field of medicines, in particular to a preparation method of trans-cefuroxim derivatives. Background technique [0002] Cefuroxime sodium (ester) is the most representative product in the second-generation cephalosporin products. With the continuous improvement of drug regulatory requirements, it is necessary to conduct corresponding research on impurities that may be produced or degraded during the production process of drugs. The structural formula of the impurity. The preparation of impurities has always been a difficult point in the process of drug research and development. Cefuroxime trans impurities were usually obtained by liquid phase separation. It has the disadvantages of extremely high cost and low yield, which leads to a very high price of trans impurities, which is not conducive to in-depth research on impurities of raw materials. Contents of the invention [0003] The purpose of the present inve...

Claims

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Application Information

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IPC IPC(8): C07D501/22C07D501/06
Inventor 蓝广忠曾建江池鲤琼王宝陈剑明王雄强
Owner GUANGDONG LIGUO PHARMACY
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