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Chemical synthesis method of valnemulin hydrochloride

A technology of vonimulin hydrochloride and chemical synthesis, applied in the directions of organic chemistry, thioether preparation, etc., can solve the problems of difficult recovery, high price of palladium carbon, increase cost, etc., and achieve the effect of easy reaction.

Active Publication Date: 2012-09-19
武汉回盛生物科技股份有限公司
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Problems solved by technology

The shortcoming of this method is that the methanol solution of HCl is used when pleuromutilin is chlorinated, which increases the corrosivity to equipment; Palladium-carbon catalyst is used when dealing with allyl protecting groups, and the price of palladium-carbon is too high and difficult to recycle , which increases the cost of the final product

Method used

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  • Chemical synthesis method of valnemulin hydrochloride
  • Chemical synthesis method of valnemulin hydrochloride

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Embodiment 1

[0019] A kind of chemical synthesis method of warnemulin hydrochloride, the steps are as follows:

[0020] (1) Refining of pleuromutilin

[0021] First, dissolve 250 g of pleuromutilin in 2000 mL of methyl tert-butyl ether, and stir to dissolve. Then add 50 g of activated carbon, stir at room temperature for 3 hours to decolorize, filter out the activated carbon, and when the filtrate is heated and concentrated to about 500 mL, a large amount of crystals precipitate out, stop heating, cool to room temperature, and then continue to stir for 4 hours. After the crystals were centrifuged, they were dried to obtain 220 g of fine pleuromutilin (yield 88%).

[0022] (2) Synthesis of p-toluenesulfonyl pleuromutilin (3)

[0023] Dissolve 20 g (0.105 mol) of p-toluenesulfonyl chloride in 300 mL of methyl tert-butyl ether, stir to dissolve, then add 40 g (0.105 mol) of pleuromutilin fine product prepared in step (1), and add dropwise 30% NaOH The solution was 15 mL (0.11 mol), and the...

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Abstract

The invention discloses a chemical synthesis method of valnemulin hydrochloride, which comprises the following steps of: taking refined pleuromutilin as raw material, carrying out sulfonation by paratoluensulfonyl chloride, and reacting with dimethyl cysteamine hcl, to obtain the pleuromutilin dimethyl cysteamine substitute; reacting D-valine, methyl acetoacetate and potassium hydroxide to obtain (R)-2-(1-methoxycarbonyl group-2-allyl) amino-3-methyl potassium butyrate, activating by ethyl chloroformate and reacting with the pleuromutilin dimethyl cysteamine substitute, adjusting PH value, carrying out reverse phase extraction, and carrying out freeze-drying to obtain the valnemulin hydrochloride. The method has the advantages that due to the refining of the raw material pleuromutilin, the impurities in the product can be effectively removed, and the purifying process can be simplified from the source; the carboxyl of D-valine can be activated by the ethyl chloroformate, so that the reaction is easier to carry out; and due to the pH adjustment, the reverse phase extraction, and the freeze-drying, the product can be obtained, so that the product is stable in quality, and high in purity.

Description

technical field [0001] The invention belongs to the technical field of semi-synthesis of antibiotics, and in particular relates to a chemical synthesis method of an animal-specific antibiotic warnemulin hydrochloride. Background technique [0002] The chemical name of Valnemulin hydrochloride is: [[2-[[(2R)-2-amino-3-methyl-1-oxobutyl]amino]-1,1-dimethyl Ethyl]thio]acetic acid (3aS, 4R, 5S, 6S, 8R, 9R, 9aR, 10R)-6-vinyl decahydro-5-hydroxy-4,6,9,10-tetramethyl-1- Oxo-3a, 9-propanol-3aH-cyclopentadiene cycloocten-8-yl ester hydrochloride, the chemical structure formula is shown in 1. The molecular weight is 601.28. It is a white non-crystalline powder with strong hygroscopicity. It is soluble in water and ethanol, but almost insoluble in methyl tert-butyl ether. The melting point is 174-177°C. [0003] [0004] Warnemulin hydrochloride is a new generation of pleuromutilin semi-synthetic antibiotics, which belongs to diterpenes and belongs to the same class of drugs as ti...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C323/52C07C319/20
Inventor 张卫元葛健薛克友陈翠兰刘国庆
Owner 武汉回盛生物科技股份有限公司
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