Preparation method of valnemulin hydrochloride

A technology of vornimulin hydrochloride and acetic acid, which is applied in the field of preparation of vornimulin hydrochloride, can solve the problems of easily polluting the environment, difficult regeneration of palladium catalysts, etc., and achieves the effects of reducing environmental pollution, less solvent, and easy mass production.

Inactive Publication Date: 2011-10-26
HUBEI SHENZHOU CHEM
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  • Abstract
  • Description
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Problems solved by technology

Although the yield of this method can be increased by 5-8%, palladium is not easy to regenerate as a catalyst, and it is easy to pollute the environment

Method used

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  • Preparation method of valnemulin hydrochloride
  • Preparation method of valnemulin hydrochloride
  • Preparation method of valnemulin hydrochloride

Examples

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Embodiment 1

[0015] Preparation of 2-(4-methylbenzenesulfonyloxy)acetic acid (3aS, 4R, 5S, 6S, 8R, 9R, 9aR, 10R)-6-vinyldecahydro-5-hydroxy-4,6,9, 10-Tetramethyl-1-oxo-3a,9-propanol-3aH-cyclopentacycloocten-8-yl ester (substance 3 in the scheme).

[0016] Dissolve 75.7 g of pleuromutilin in methanol (200 ml). Water (40ml) was added, cooled in an ice-water bath to 0°C and stirred for 15min. A mixture of 42.0 g of p-toluenesulfonyl chloride and water (120 ml) was added dropwise. After dropping, stir at 100°C for 1000min. Cool to 0°C in an ice-salt bath, slowly drop into 10mol / L sodium hydroxide aqueous solution (50ml), heat to reflux for 0.5h and then cool to room temperature. Cool in an ice-salt bath to 0°C, add water (40ml), filter, wash the filter cake with water (20ml×3) and cold methanol (20ml×3) in sequence, and dry at 100°C to obtain a white solid (substance 3 in the reaction formula) .

[0017] Preparation of [(2-amino-1,1-dimethylethyl)thio]acetic acid (3aS, 4R, 5S, 6S, 8R, 9R,...

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Abstract

The invention relates to a preparation method of valnemulin hydrochloride. The preparation method comprises the following steps: reacting pleuromutilin with p-toluenesulfonyl chloride, substituting with 1-amino-2-methyl propyl-2-mercaptan hydrochloride so as to obtain [(2-amino-1,1-dimethyl S, 6S, 8R,9R, 9aR, 10R)-6-vinyl decahydro-5-hydroxyl-4,6,9,10-tertamethyl-1-oxo-3a, 9-propanol-3aH-cyclopentacyclooctene-8-yl ester for later use; reacting D-valine with methyl acetoacetate; synthesizing the product with isobutyl chloroacetate so as to generate anhydride; and reacting anhydride with [(2-amino-1,1-dimethyl ethyl) sulfenyl] acetic acid (3aS, 4R, 5, 6S, 8R,9R, 9aR, 10R)-6-vinyl decahydro-5-hydroxyl-4,6,9,10-tertamethyl-1-oxo-3a, 9-propanol-3aH-cyclopentacyclooctene-8-yl ester so as to generate amide, and then carrying out deprotection with hydrochloric acid so as to prepare valnemulin hydrochloride. The method has the advantages that (1) reaction temperature is mild, thereby being applicable to large-scale production; (2) post-treatment is simple, thereby directly obtaining the product; (3) used solvents are less, thereby reducing environmental pollution; and (4) the valnemulin hydrochloride content and yield of the obtained product are high.

Description

technical field [0001] The invention relates to a preparation method of antibiotics, in particular to a preparation method of warnemulin hydrochloride. Background technique [0002] Molecular formula of valnemulin hydrochloride: [0003] [0004] The chemical name is [[2-[[(2R)-2-amino-3-methyl-1-oxobutyl]amino]-1,1-dimethylethyl]thio]acetic acid 3aS, 4R, 5S, 6S, 8R, 9R, 9aR, 10R)-6-vinyl decahydro-5-hydroxyl-4,6,9,10-tetramethyl-1-oxo-3a,9-propanol-3aH- Cyclopentadienyl cycloocten-8-yl ester hydrochloride. [0005] Warnimulin hydrochloride is a pleuromutilin semi-synthetic broad-spectrum new animal-specific antibiotic, used for the prevention and treatment of streptococcus suis, porcine enzootic pneumonia, swine dysentery, porcine spirochete, porcine proliferative enteritis and chicken Chicken diseases such as chronic respiratory tract infection. On September 9, 2010, the Ministry of Agriculture Announcement No. 1457 approved that the raw material and preparation of ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C323/52C07C319/20
Inventor 闵江华刘登才黄剑雄
Owner HUBEI SHENZHOU CHEM
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