Method for synthesizing 2 - amido - 9 - capric olefine acid

A technology of optical activity and synthesis method, applied in the synthesis field of optically active 2-amino-9-decenoic acid, can solve the problems of high cost and use price, and achieve the effects of improving synthesis efficiency, reducing cost and shortening synthesis process
CN101092368AInactive Publication Date: 2007-12-26上海药明康德新药开发有限公司
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Patent Information

Authority / Receiving Office
CN · China
Current Assignee / Owner
上海药明康德新药开发有限公司
Publication Date
2007-12-26
Estimated Expiration
Not applicable · inactive patent

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Abstract

This invention relates to a method for preparing optically active 2-amino-9-decenoic acid. The method comprises: attacking chiral 6-oxy-piperidine-2-carboxylate with Grignard reagent of crotyl bromide to obtain chiral 2-amino-6-oxy-9-decadienoate, reducing to convert carbonyl into methylene and obtain chiral or racemized 2-amino-9-decadienoate, and hydrolyzing to obtain optically active 2-amino-9-decenoic acid. The method overcomes the problems of long synthesis route, low yield and expensive chiral catalyst or resolution reagent faced by the present method. The method in this invention has such advantages as simple route, reasonable process, low cost, and high yield, and is suitable for mass production.
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Description

Technical field:

[0001] The invention relates to a method for synthesizing optically active 2-amino-9-decenoic acid with terminal double bonds. Background technique:

[0002] Many protease inhibitors are composed of polypeptides or macrocyclic polypeptides. Optically active long-chain amino acids with terminal double bonds have also appeared in recent years as a component of polypeptides or macrocyclic polypeptides. With the metal metathesis reaction As organic synthesis becomes more and more widely used, such molecules are becoming more and more important in the synthesis of macrocyclic peptides. 2-Amino-9-decenoic acid has been reported in the literature to have good physiological activity.

[0003] In current literature reports, there are two methods for the synthesis of chiral 2-amino-9-decenoic acid: the first method is to obtain a A chiral intermediate, the chiral 2-amino-9-decenoic acid can be obtained after removing the prosthetic group (Tetrahedron Lett.1984, 5525...

Claims

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