Optically active beta-lactam synthesis method

Through the synthesis route of chiral amines, the problems of difficult separation and purification and many by-products in the synthesis of β-lactams are solved, efficient and low-cost synthesis of optically active β-lactams is achieved, the steps are simplified and the diastereomeric efficiency is improved. Selective, suitable for industrial production.

CN104327110AInactive Publication Date: 2015-02-04JINGGANGSHAN UNIVERSITY
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Patent Information

Application Number
CN201410488558.9
Authority / Receiving Office
CN · China
Patent Type
Applications(China)
Current Assignee / Owner
Filing Date
2014-09-22
Publication Date
2015-02-04
Estimated Expiration
Not applicable · inactive patent

AI Technical Summary

Technical Problem

Existing β-lactam synthesis methods have problems such as difficult separation and purification, many by-products, multiple synthesis steps, high costs, and poor diastereoselectivity. In particular, it is difficult to effectively synthesize chiral lactams, resulting in low production efficiency and increased costs.

Method used

Using chiral amines as starting materials, the reaction is carried out through a specific synthetic route, including the reaction of phenyl-substituted α-phenylethylamine with benzaldehyde, followed by treatment with acetoxyacetyl chloride and a base, followed by crystallization and chromatographic separation, Finally, the chiral group is removed by oxidation to obtain a highly optically active β-lactam.

Benefits of technology

It achieves simplified synthesis steps, reduces separation steps, improves diastereoselectivity, obtains highly optically active β-lactam directly through crystallization and chromatographic separation, reduces production costs and by-products, and is suitable for industrial production.

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Abstract

The present invention provides an optically active beta-lactam synthesis method, and optically active beta-lactam can be prepared from commercially available products as raw materials by 5 steps of synthesis; the optically active beta-lactam synthesis method can be used for the synthesis of side chain of paclitaxel and docetaxel. The synthesis method uses a chiral amine as a raw material, the chiral amine has good diastereoselectivity, and can effectively and directly crystallize and separate diastereomers to obtain the optically active beta-lactam, the separation steps are less, and comprise two separate steps of one time of recrystallization and one time of chromatographic separation. In addition, a chiral group can be easily oxidized for removal, and the method is an efficient method for the synthesis of the optically active beta-lactam. The method has the advantages of simple synthesizing steps, less separation steps comprising just one time of crystallization, and one time of column chromatography, and prospect of industrialization application.
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