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Method for producing d-biotin

A technology of biotin and synthesis method, applied in the direction of organic chemistry, etc., can solve the problems of long synthesis route and low total yield, and achieve the effect of simple operation, high yield and shortened process route

Inactive Publication Date: 2004-08-18
MIANZHU HANWANG YELLOW PHOSPHORUS SICHUAN CHINA
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Problems solved by technology

[0007] In order to overcome the shortcomings of long synthetic routes and low total yields in the prior art and to fill in the gaps in China, the present invention provides a new synthetic process for the production of d-biotin
Sternbach synthetic method and the present invention belong to similar synthetic technique

Method used

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  • Method for producing d-biotin
  • Method for producing d-biotin

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Embodiment Construction

[0018] The present invention utilizes imidazolinone-cis-dicarboxylic acid with concentrated sulfuric acid as a catalyst to generate racemic monoester through esterification reaction with methanol, splits it with right amine, and selectively reduces the monoester group with sodium borohydride Obtain the lactone with the desired absolute configuration, then replace the oxygen with sulfur in potassium ethyl thioacetate to obtain the thiolactone, then use the Grignard reaction to introduce the side chain, and obtain (3aR, 6aR) by carbon dioxide and concentrated sulfuric acid -1,3-dibenzyltetrahydro-1H-thieno[3.4-d]imidazol-2-(3H)-one-enoic acid, then use palladium-carbon as a catalyst to hydrogenate dibenzyl biotin, and then in The pure, optically active d-biotin can be obtained after removing two benzyl groups in hot hydrobromic acid.

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Abstract

The production process of d-biotin is one improvement of Sternbach synthesis. The production process includes: the esterification of imidazolone-cis-dicarboxylic acid and methanol in the presence of concentrated sulfuric acid as catalyst to produce racemic monoester; resolution with dextramine; selective reduction of the monoester radical in the resolved matter with sodium borohydride to obtain lactone in required absolute configuration; substitution of oxygen with sulfur in potassium ethyl thioacetate to obtain thiolactone; Grignard reaction to introduce side chain and to obtain keto-olefine acid; hydrogenation with Pd-C catalyst to obtain dibenzyl biotin; and elimination of two benzyl radicals in hot hydroboromic acid to obtain pure optically active d-biotin. The said technological process has short technological path, low cost, simple operation and high yield.

Description

technical field [0001] The invention relates to a production method of d-biotin. Background technique [0002] d-biotin, also known as vitamin H (VH), is one of the varieties with the smallest yield among the thirteen vitamin products. It is widely used in medical treatment, multidimensional preparations and feed additives, and is necessary for the growth and metabolism of living substances. The trace amount of organic active substances has been included in the 24th edition of the United States Pharmacopoeia (USP24) and the European Pharmacopoeia (EP1999). Its chemical name is: [3aS-(3aα, 4β, 6aα)]-hexahydro-2-oxo-1-H-thieno[3.4-d]imidazole-4-pentanoic acid; English name: biotin or d -biotin, English chemical name: [3aS-(3aα, 4β, 6aα)]-Hexahydro-2-oxo-1H-thieno[3.4-d]imidazote-4-Valericacid. [0003] d-Biotin was discovered in 1901. In 1936, the active factor was isolated from egg yolk for the first time and named as biotin. Its molecular formula was established in 1941 an...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D495/04
Inventor 肖代礼刘英
Owner MIANZHU HANWANG YELLOW PHOSPHORUS SICHUAN CHINA
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