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Method for synthesizing valnemulin hydrochloride

A technology for the synthesis of warnemulin hydrochloride and its synthesis method, which is applied in the field of synthesis of warnemulin hydrochloride, can solve the problems that it cannot be used as medicine, is not suitable for industrial production, and does not exceed 93%, and achieves loss reduction and volatilization. The effect of reducing the property and increasing the yield

Inactive Publication Date: 2010-06-16
SHANDONG SHENGLI CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] The shortcoming of this method is that the crude product purity of gained vonemulin is generally not more than 93%, can not be used as medicine, is not suitable for industrialized production

Method used

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  • Method for synthesizing valnemulin hydrochloride
  • Method for synthesizing valnemulin hydrochloride
  • Method for synthesizing valnemulin hydrochloride

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] Add 37.85 g of pleuromutilin and 150 ml of acetone into a 250 ml three-necked flask equipped with a mechanical stirrer and a thermometer, and stir to dissolve it. Place the three-necked bottle in a low-temperature tank and cool down to 0°C. Add 19.06g of p-toluenesulfonyl chloride and 15ml of 40wt% NaOH, and stir the reaction for 20min. After the reaction, the solvent was concentrated to dryness to obtain pleuromutilin.

[0045] Add 53.2g pleuromutilin sulfonated, 14.2g dimethylcysteamine hydrochloride, 1.2g tetrabutylammonium bromide, 30ml 10N NaOH solution in a 500ml three-necked flask equipped with mechanical stirring, thermometer and reflux device and 100ml tert-butyl methyl ether. Heat and stir at 53° C. for 1 h, detect by TLC, and add 250 ml of water to the three-neck flask if the reaction is complete. The reaction temperature was lowered to 0°C, and after stirring at this temperature for 30 minutes, a precipitate was found to be formed, filtered, and the filte...

Embodiment 2

[0051] Add 30.1 g of pleuromutilin and 180 ml of ethanol into a 250 ml three-necked flask equipped with a mechanical stirrer and a thermometer, and stir to dissolve it. Place the three-necked bottle in a low-temperature tank and cool down to -5°C. 15.1 g of p-toluenesulfonyl chloride and 12 ml of 40 wt% NaOH were added, and the reaction was stirred for 30 min. After the reaction, the solvent was concentrated to dryness to obtain a solid product.

[0052] Add 100g of pleuromutilin, 32g of dimethylcysteamine hydrochloride, 3g of cetyltrimethylammonium bromide, and 50ml of 10N NaOH into a 500ml three-necked flask equipped with mechanical stirring, a thermometer and a reflux device solution and 300ml 2-methylisoamylone. Heat and stir at 55° C. for 1 h, and detect by TLC. If there are no spots of dimethylcysteamine hydrochloride, the reaction is complete; after the reaction, the organic phase is directly used for the synthesis of warnemulin hydrochloride.

[0053] Add 8g of soli...

Embodiment 3

[0058] Except that butyl acetate is used as solvent when preparing ATAM, others are the same as Example 2.

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Abstract

The invention discloses a method for synthesizing valnemulin hydrochloride. The method taking pleuromytilin a raw material comprises the following steps: synthesizing sulfonated pleurin; then, preparing 14-O-[(1-amido-2-methyl-propyl-2-yl)acetyl] mutelin by the sulfonated pleurin; synthesizing D-valine deng salt by D-valine; and finally, mixing the 14-O-[(1-amido-2-methyl-propyl-2-yl)acetyl] mutelin, the D-valine deng salt, N-methylmorpholine and allyl chloroformate by a certain sequence and a certain condition and reacting to generate mixed anhydride so as to obtain the valnemulin hydrochloride by the subsequent steps of acidylating, hydrolyzing, separating, drying and the like. The invention realizes the accurate control of the reaction by controlling the technological parameters of the reaction temperature, the drying condition, the reaction pH and the like and enhances the reaction efficiency and the quality and the purity of a product effectively. The obtained valnemulin hydrochloride can be used for medicines and meets the market requirement.

Description

technical field [0001] The present invention relates to a kind of synthetic method of warnemulin hydrochloride, specifically, relates to a kind of 14-O-[(1-amino-2-methylpropyl-2-yl) acetic acid base] Lin and D-valine Deng salt as raw materials for the synthesis of warnemulin hydrochloride. Background technique [0002] Valnemulin Hydrochloride is a new generation of pleuromutilin semi-synthetic antibiotics for animals. It belongs to diterpenes and belongs to the same class of drugs as tiamulin. It is mainly used abroad to prevent mycoplasma disease and Gram-positive bacterial infection in pigs, cattle, sheep and poultry. It has the characteristics of broad spectrum, strong antibacterial activity, excellent pharmacokinetic characteristics, low residue and safety. In 1999, it was approved by the European Union for the prevention and treatment of swine dysentery caused by Brachyspira hyodysenteriae infection and swine enzootic pneumonia caused by Mycoplasma pneumoniae infecti...

Claims

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Application Information

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IPC IPC(8): C07C323/52C07C319/20
Inventor 雷宪军孔凡亭胡江林王斌李明
Owner SHANDONG SHENGLI CO LTD
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