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A kind of preparation method of cefditoren pivoxil intermediate

A technology for cefditoren pivoxil and intermediates, which is applied in the field of synthesis of pharmaceutical intermediates, can solve problems such as poor yield, and achieve the effects of good yield and simple process

Active Publication Date: 2016-03-23
CHENGDU YILUKANG MEDICAL TECH & SERVICE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] The object of the present invention is to overcome the shortcomings of the poor yield of the intermediate synthesis method of cefditoren pivoxil in the prior art, and provide a safe, environmentally friendly, high yield intermediate for cefditoren pivoxil suitable for industrialized large-scale production resolve resolution

Method used

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  • A kind of preparation method of cefditoren pivoxil intermediate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] 7-Phenylacetamido-3-[(Z)-2-(4-methyl-5-thiazolyl)vinyl]-4-cephalosporanic acid p-methoxybenzyl ester

[0026] Put 100L of purified water, 100L of dichloromethane, 25kg of GCLE, 8.2kg of anhydrous sodium iodide, and 14.5kg of triphenylphosphine into the reaction kettle, and react at 30°C for 1.5 hours. When the temperature was lowered to 0°C, 2% sodium hydroxide was added dropwise to adjust the pH to 7. The layers were separated, the temperature of the dichloromethane layer was lowered to -25°C, 20 kg of 4-methyl-5-thiazole formaldehyde was added, and the reaction was kept overnight. After the reaction was complete, 150 L of 5% sodium bisulfite solution was added and stirred for half an hour. The layers were separated, the dichloromethane layer was concentrated to dryness in vacuo, 200 L of methanol was added, and the mixture was stirred at 0°C for 2 hours. After centrifugation, 27.5 kg of the title compound was obtained with a yield of 95.5%.

Embodiment 2

[0028] 7-Phenylacetamido-3-[(Z)-2-(4-methyl-5-thiazolyl)vinyl]-4-cephalosporanic acid p-methoxybenzyl ester

[0029] Put 100L of purified water, 100L of chloroform, 25kg of GCLE, 8.2kg of anhydrous sodium iodide, and 14.5kg of triphenylphosphine into the reaction kettle, and react at 30°C for 1.5 hours. When the temperature was lowered to 0°C, 2% sodium hydroxide was added dropwise to adjust the pH to 7. The layers were separated, the temperature of the dichloromethane layer was lowered to -25°C, 20 kg of 4-methyl-5-thiazole formaldehyde was added, and the reaction was kept overnight. After the reaction was complete, 150 L of 5% sodium bisulfite solution was added and stirred for half an hour. The layers were separated, the chloroform layer was concentrated to dryness in vacuo, 200 L of methanol was added, and the mixture was stirred at 0°C for 2 hours. After centrifugation, 27.2 kg of the title compound was obtained with a yield of 94.4%.

Embodiment 3

[0031] 7-Phenylacetamido-3-[(Z)-2-(4-methyl-5-thiazolyl)vinyl]-4-cephalosporanic acid p-methoxybenzyl ester

[0032] Put 100L of purified water, 100L of ethyl acetate, 25kg of GCLE, 8.2kg of anhydrous sodium iodide, and 14.5kg of triphenylphosphine into the reaction kettle, and react at 30°C for 1.5 hours. When the temperature was lowered to 0°C, 2% sodium hydroxide was added dropwise to adjust the pH to 7. The layers were separated, the temperature of the dichloromethane layer was lowered to -25°C, 20 kg of 4-methyl-5-thiazole formaldehyde was added, and the reaction was kept overnight. After the reaction was complete, 150 L of 5% sodium bisulfite solution was added and stirred for half an hour. The layers were separated, the ethyl acetate layer was concentrated to dryness in vacuo, 200 L of methanol was added, and the mixture was stirred at 0°C for 2 hours. After centrifugation, 27.7kg of the title compound was obtained with a yield of 96.2%.

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Abstract

The invention discloses a synthesis method of a drug intermediate, and particularly relates to a preparation method of a cefditoren pivoxil cephalosporins intermediate. The preparation method comprises the step of reacting through phosphorus Ylide-Wittig reaction and hydrolysis reaction by using 7-phenylacetamide-3-chloromethylcephalosporanic acid p-methoxybenzyl ester to obtain cefditoren pivoxil cephalosporins. The preparation method is simple in process, safe, environment-friendly, high in yield, and suitable for industrialized production.

Description

technical field [0001] The present invention relates to a kind of synthetic method of medicine intermediate, particularly a kind of preparation method of cefditoren pivoxil intermediate. Background technique [0002] Cefditoren pivoxil is the third-generation oral cephalosporin, pioneered by Japan's Meiji Seika Co., Ltd. It went on the market in Japan in April 1994 and in China in April 2001 under the trade name of Miac. The dosage form currently on the market in China is film-coated tablets. Indications are Staphylococcus, Streptococcus, Peptostreptococcus, Branham catarrhalis, Propionibacterium acnes, Escherichia coli, Citrobacter, Klebsiella, Enterobacter, Serratia The following infections caused by bacteria sensitive to cefditoren in the genus Proteus (Proteus mirabilis, Proteus vulgaris), Morganella, Providencia, Haemophilus influenzae, and Bacteroides: ①Folliculitis, furuncle, furunculosis, carbuncle, contagious impetigo, erysipelas, cellulitis, lymphangio (node) in...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D501/24C12P35/02
Inventor 骆均勇彭超
Owner CHENGDU YILUKANG MEDICAL TECH & SERVICE
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