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Valnemulin synthesis method

A Vonimulin and synthetic method technology, applied in bulk chemical production, sulfide preparation, organic chemistry and other directions, can solve the problems of complex process, low yield and high cost, and achieve simple process operation, high yield, low cost effect

Inactive Publication Date: 2011-03-30
BEIJING ZHONGMU TECH SERVICE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The existing bibliographical report of the synthetic existing bibliographical information of warnimulin, the shortcoming of its synthesis is: 1) be mostly the synthetic method (Berner H, VypleR H; [P]EP0153277A2,1985) in last century 80's or early 90's, synthetic route It is long, the yield is low, the process is more complicated, and the starting materials are difficult to find in China, or the price is high, or it is difficult to synthesize (Macha, I.[P]EP0421364A2, 1990)
Therefore, there are disadvantages such as high cost and imperfect technology in the mass production of Wonimulin in China, which cannot meet the growing commercial demand.

Method used

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Examples

Experimental program
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Effect test

Embodiment 1

[0031] (1) Synthetic compound pleuromutilin sulfonate (2):

[0032]

[0033] Instruments: 1000mL three-necked flask with reflux condenser, thermometer and addition funnel. Add methyl tert-butyl ether (200mL), water (40mL) into the bottle, and cool to 0°C in an ice-water bath, then add pleuromutilin (1) (75.7g), and stir at 0-3°C for 15 minutes . Add p-toluenesulfonyl chloride (42.0 g), tert-butyl methyl ether (160 mL) and water (120 mL) into the dropping funnel, and slowly drop them into the reaction flask. After the dropwise addition, the resulting suspension was stirred at room temperature for 10 minutes, cooled to 0° C. with an ice-salt bath, and 1N NaOH (50 mL) was slowly added dropwise to the reaction solution. The resulting mixture was heated to reflux for 2 hours. The reactant was cooled to 0°C in ice-brine, and water (400 mL) was added. A large amount of solid formed which was filtered. The solid was filtered out with water, washed with cold ether, and dried to...

Embodiment 2

[0044] (1) Synthetic compound pleuromutilin sulfonate (2):

[0045]

[0046] Instruments: 1000mL three-necked flask with reflux condenser, thermometer and addition funnel. Add methyl tert-butyl ether (200mL), water (40mL) into the bottle, and cool to 0°C in an ice-water bath, then add pleuromutilin (1) (75.7g), and stir at 0-3°C for 15 minutes . Add methanesulfonyl chloride (38.0g), diethyl ether (160mL) and water (120mL) into the dropping funnel, and slowly drop them into the reaction flask. After the dropwise addition, the resulting suspension was stirred at room temperature for 10 minutes, cooled to 0° C. with an ice-salt bath, and 1N KOH (50 mL) was slowly added dropwise to the reaction solution. The resulting mixture was heated to reflux for 2 hours. The reactant was cooled to 0°C in ice-brine, and water (400 mL) was added. A large amount of solid formed which was filtered. The solid was filtered out with water, washed with cold ether, and dried to obtain 46.6 g o...

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Abstract

The invention discloses a valnemulin synthesis method which comprises the following steps of: 1. pleuromutilin sulphonic acid ester synthesis: using pleuromutilin as raw materials to react with sulfonic acid chloride under the alkaline condition for converting the pleuromutilin into pleuromutilin sulphonic acid ester; 2. sulpho-pleuromutilin synthesis: using penicillamine to substitute sulphonic acid ester in the product in the step 1 under the alkaline condition to obtain sulpho-pleuromutilin; 3. amino-protected D-R-valine synthesis; and 4. valnemulin synthesis. The mainly used raw materials of the valnemulin synthesis method are fermentation products of the pleuromutilin and cysteine which can be easily obtained in the market and have low cost, and in addition, the valnemulin synthesis method has simple process operation, has no danger, has the characteristics of low cost, high yield and the like, is applicable to enlargement and industrial production and has industrialization value.

Description

technical field [0001] The present invention relates to a new synthetic method of warnemulin. Background technique [0002] 2-(2-((R)-2-amino-3-methylbutyrylamino)-1,1-dimethylethyl)mercapto)acetic acid, (3aS, 4R, 5S, 6S, 8R, 9R, 9aR,10R)-octahydro-5,8-dihydroxy-4,6,9,10-tetramethyl-6-vinyl-3a,9-propane-3aH-cyclopentacyclooctene-1(4H) -Keto-8-ester is available under the trade name Valnemulin. Vernimulin is a new generation of pleuromutilin (Pleuromutilin) ​​semi-synthetic antibiotics. It belongs to diterpenes and belongs to the same class of drugs as tiamulin. It is an animal-specific antibiotic and is mainly used to prevent and treat pigs, cattle, sheep and Mycoplasmosis and Gram-positive bacterial infections in poultry. In 1999, it was approved by the European Community for the prevention and treatment of swine dysentery caused by Brachyspira hyodysenteriae infection and swine enzootic pneumonia caused by Mycoplasma pneumoniae infection. In January 2004, it was approv...

Claims

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Application Information

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IPC IPC(8): C07C323/52C07C319/20
CPCY02P20/55
Inventor 陈怀谷冯德鑫李新乐潘强王峥
Owner BEIJING ZHONGMU TECH SERVICE
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