Preparation method of cefdinir

A technology of cefdinir and 7-AVCA, applied in the field of preparation of cefdinir, can solve the problems of product yield and finished product quality influence, cost and environmental pollution, low synthesis yield, etc. The effect of recycling and reducing production costs

Active Publication Date: 2009-10-28
ZHEJIANG ANGLIKANG PHARMA
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0011] No matter which of the above-mentioned preparation methods is adopted, the following problems will exist: the one, the synthesis yield is low, and the reagents used are many and expensive, which will bring problems such as cost and environmental pollution; Yield and finished product quality have certain influence

Method used

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  • Preparation method of cefdinir
  • Preparation method of cefdinir
  • Preparation method of cefdinir

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] a. Put 20 g of 7-AVCA, 36 g of cefdinir active methyl ester, 100 ml of water, and 200 ml of methanol into a 500 ml three-necked flask, and dropwise add 20 g / 50 ml of tri-n-butylamine / methanol mixture at -10 ° C, and the addition is complete , Insulate and react at -10°C for 24 hours, take samples for HPLC until the 7-AVCA residue is qualified, adjust ph=5 with dilute hydrochloric acid, recover most of the methanol under reduced pressure; add 100ml of water and 200ml of ethyl acetate, stir for 30 minutes, and let it stand for 30 minutes minute. Separate the water layer, add 50ml of water to the oil layer, stir for 30 minutes, and let stand for 30 minutes. The solvent is recovered from the oil layer to obtain the by-product mercaptobenzothiazole. Add 5 g of activated carbon to the combined water layer, decolorize at 25°C for 1 hour, filter, adjust the pH of the filtrate to 3.0 with dilute hydrochloric acid at 25°C, cool down to 5°C and stir for 1 hour, and filter to obta...

Embodiment 2

[0037] Put 20 grams of 7-AVCA, 36 grams of cefdinir active methyl ester, 100 ml of water, and 200 ml of acetone into a 500 ml three-necked flask, add 20 g / 50 ml of tri-n-butylamine / acetone mixture dropwise at -5 ° C, and after the addition, - Incubate at 5°C for 24 hours, take a sample for HPLC until the 7-AVCA residue is qualified, and the post-processing steps are the same as in Example 1.

Embodiment 3

[0039] Put 20 grams of 7-AVCA, 36 grams of cefdinir active methyl ester, 100 ml of water, and 200 ml of ethanol into a 500 ml three-neck flask, add 20 g / 50 ml of triethylamine / ethanol mixture dropwise at 0°C, and drop it at -5°C Incubate the reaction for 24 hours, take a sample for HPLC until the 7-AVCA residue is qualified, and the post-processing steps are the same as in Example 1.

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Abstract

The invention relates to a preparation method of cefdinir, comprising the following steps: reacting 7-amino-3-vinyl-8-oxy-5-thia-1- nitric heterocyclic dicyclo[4.2.0]octyl-2-en-2-carboxylic acid with (Z)-2-(2-aminothiazole-4-yl)-2-acetoxy imino thioacetic acid (S-2-benzothiazole)ester in the presence of organic base at low temperature; extracting, adjusting p H value, preparing the intermediate of the cefdinir, removing the ester-group protective group of the intermediate of the cefdinir to obtain the cefdinir. The preparation method uses the low-temperature reaction technique, capable of increasing the reaction yield and reducing the impurities generated by the high temperature reaction. The hydrolysis and crystallization process is very easily controlled. The used alcohols, ketones or esters solvent is easily recovered, thus the production cost and the three-wastes drain are reduced, therefore the pollution to the environment is reduced. The preparation method of cefdinir is suitable for large-scale production.

Description

technical field [0001] The invention relates to a preparation method of cefdinir, which belongs to the technical field of cefdinir synthesis in the chemical pharmaceutical industry. [0002] The structure of cefdinir is as follows: [0003] [0004] Formula I Background technique [0005] Cefdinir (Cefdinir) is an antibiotic produced by Teng Ze Pharmaceutical Co., Ltd. in Japan. This product has antibacterial activity against Gram-positive bacteria and negative bacteria, and is stable to most β-lactamases, so many Microorganisms resistant to penicillins and cephalosporins are sensitive to this product. It is used for respiratory tract, ENT, urinary system, skin soft tissue and gynecological infections, etc. It has a broad-spectrum antibacterial effect and has achieved good clinical results. [0006] The preparation method of cefdinir is mainly as follows at present: [0007] Route 1: Condensation reaction between different types of active intermediates 1 and compound ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D501/22C07D501/06A61P31/04
CPCY02P20/55
Inventor 王明光方南平叶树祥徐成苗魏肖波
Owner ZHEJIANG ANGLIKANG PHARMA
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