Method for preparing D-(+)-biotin intermediate

A technology of biotin and intermediates, applied in chemical instruments and methods, chemical/physical processes, physical/chemical process catalysts, etc., can solve the problem of poor stability and reproducibility of carbonyl reduction coupling reaction, harsh synthesis conditions, mercapto marine products Low toxicity and other problems, to achieve the effect of relatively low toxicity and easy purchase
CN101735242BActive Publication Date: 2012-06-27安徽泰格生物技术股份有限公司
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Patent Information

Authority / Receiving Office
CN · China
Patent Type
Patents(China)
Current Assignee / Owner
安徽泰格生物技术股份有限公司
Publication Date
2012-06-27

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Abstract

The invention provides a method for preparing a D-(+)-biotin intermediate. The method comprises the steps of: taking L-cysteine monohydrochloride as a starting material; using benzaldehyde and sodium cyanate as a ring closure reagent to synthesize (7aR)-3-phenyl-6-benzyl-1H, 3H-imidazo[1, 5-C]thiazole-(6H, 7aH)-5, 7-dione through the cyclization; then utilizing benzyl bromide to perform benzyl protection on N atoms; then taking zinc as a reducing agent to perform ring-opening synthesis on N, N-dibenzyl-L-sulfhydryl hydantoin; introducing a side chain through an esterification reaction with monomethyl adipate acyl chloride; and taking titanium as the reducing agent to perform reductive ring closure to generate the intermediate. According to the method, the cheap and readily available sodium cyanate is used as the ring closure reagent to replace sodium isocyanate which is toxic and difficult to purchase in an original method, reaction conditions are optimized and reaction order is adjusted, so the disadvantages of harsh reaction conditions and low yield in the original method of ring opening first and then benzyl protection are overcome by the method of performing benzyl protection on the N atoms of an imidazole part first and then performing ring opening; and the total yield reaches 34.0-38.0 percent.
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Description

technical field

[0001] The present invention relates to a compound synthesis method, in particular to a biotin intermediate: (6aR)-1,3-dibenzyl-4-(4-methoxycarbonylbutyl)-dihydro-thieno Process for the preparation of [3,4-d]imidazol-2-one. It belongs to the field of mechanochemical synthesis. Background technique

[0002] (6aR)-1,3-Dibenzyl-4-(4-methoxycarbonylbutyl)-dihydro-thieno[3,4-d]imidazol-2-one has the following structural formula:

[0003]

[0004] The compound is a key intermediate for the synthesis of biotin by a stereospecific method. Under the induction of a chiral carbon, it is hydrogenated in cis, and then debenzylated and hydrolyzed to obtain D-biotin.

[0005] Stereospecific synthesis of biotin using L-cysteine ​​or L-cystine and other substances with optical activity as the starting material is a relatively stable synthesis method, which is different from the traditional Hoffmann-La Roche production technology. Compared with this method, it has many a...

Claims

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