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Method for preparing valnemulin

A technology for vornimulin and pleuromutilin, which is applied in the field of preparation of vornimulin, can solve the problems of environmental hazards of tosylate, large loss of pleuromutilin, influence on yield of intermediates, etc. loss, increase synthesis yield, and improve product quality

Inactive Publication Date: 2008-12-10
江苏赛奥生化有限公司
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Problems solved by technology

The disadvantages of the above-mentioned preparation process are: first, pleuromutilin is involved in every step of the reaction in the preparation process, resulting in a large loss of pleuromutilin, which reduces the yield; second, the use of sulfonated pleuromutilin and 1,1 -Dimethyl-2-aminoethanethiol reaction, its by-product p-toluenesulfonate will cause great harm to the environment; the third, directly adopt 1,1-dimethyl-2-aminoethanethiol and sulfonated In the pleuromutilin reaction, there is competition between the amino group and the sulfhydryl group, which not only increases the side reaction, but also affects the yield of the intermediate

Method used

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Embodiment Construction

[0017] A preparation method of warnimulin, comprising the following steps:

[0018] (1) Preparation of pleuromutilin chloride: prepare 1400ml of 5M HCl-MeOH solution, slowly add dropwise at -35-+35 degree to 280ml THF solution containing 50.0g of pleuromutilin, continue to react for 5-10 hours after adding , and concentrated under reduced pressure to obtain 49.25 grams of pleuromutilin chloride, with a weight yield of 98.5% (the weight yield of pleuromutilin chloride to pleuromutilin).

[0019] (2) Preparation of N-allyloxycarbonyl valine: Dissolve 20 grams of valine in 170 ml of dichloromethane, cool to 0 degrees, add dropwise 85 ml of dichloromethane containing 21 mL of allyl chloroformate under stirring solution, stirred at room temperature for 2 hours until the reaction was complete, washed with 1M hydrochloric acid, dried the organic layer with anhydrous sodium sulfate, and concentrated to obtain 33.79 grams of N-allyloxycarbonyl valine, with a weight yield of 168.95% (N-...

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Abstract

The invention discloses a method for preparing valnemulin. The method comprises the following steps of: preparation of chloridized pleuromutilin, preparation of N-allyloxycarbonyl-valine; preparation of 1, 1-dimethyl-2-(N-allyloxycarbonyl valyl amino) ethanethiol and preparation of the valnemulin. The method can effectively improve the product quality and the yield.

Description

Technical field: [0001] The invention relates to a preparation method of warnemulin. Background technique: [0002] Valnemulin is a new type of pleuromutilin semi-synthetic broad-spectrum animal-specific antibiotics for the prevention and treatment of streptococcus suis, porcine enzootic pneumonia, swine dysentery, porcine spirochete and porcine proliferative enteritis, chicken Diseases such as chronic respiratory infections. The preparation of warnimulin has been reported in the literature. They all use pleuromutilin as a raw material. The intermediate is prepared by reacting the prime with 1,1-dimethyl-2-aminoethanethiol, and then the intermediate is reacted with valine whose amino group is protected and the carboxyl group is activated, and vonemulin is obtained after deprotection. The disadvantages of the above-mentioned preparation process are: first, pleuromutilin is involved in every step of the reaction in the preparation process, resulting in a large loss of pleuro...

Claims

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Application Information

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IPC IPC(8): C07C323/52C07C319/20
Inventor 陈剑慧韩勤更邓京沈敏祥沈春梅
Owner 江苏赛奥生化有限公司
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