A highly efficient way to recycle inactive stereoisomers of Bedaquiline into two previous intermediates via base-catalyzed Csp3-Csp3 bond cleavage

De-Long Kong Ye Huang Lai-Yang Ren Wen-Hua Feng

Citation:  De-Long Kong, Ye Huang, Lai-Yang Ren, Wen-Hua Feng. A highly efficient way to recycle inactive stereoisomers of Bedaquiline into two previous intermediates via base-catalyzed Csp3-Csp3 bond cleavage[J]. Chinese Chemical Letters, 2015, 26(6): 790-792. doi: 10.1016/j.cclet.2015.04.013 shu

A highly efficient way to recycle inactive stereoisomers of Bedaquiline into two previous intermediates via base-catalyzed Csp3-Csp3 bond cleavage

    通讯作者: Ye Huang,
    Wen-Hua Feng,
  • 基金项目:

    Technology Major Project of China (No. 521042). (No. 521042)

摘要: Bedaquiline is a new medicine for pulmonary multi-drug resistant tuberculosis (MDR-TB), which is a pure enantiomer with two chiral centers. The current industrial preparation process requires the separation of active Bedaquiline from a mixture of four isomers. Obviously, direct dispose of the other three undesired stereoisomers will cause significant waste and increase the unnecessary cost of production. Here, we developed an efficient, facile and scalable process for recycling the inactive stereoisomers of Bedaquiline. All these inactive stereoisomers could be recycled by their conversion to two important intermediates in the Bedaquiline synthesis via a base-catalyzed Csp3-Csp3 bond cleavage of a benzyl alcohol intermediate. And the precise conditions and mechanism of the base-catalyzed cleavage reaction were discussed.

English

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  • 发布日期:  2015-04-18
  • 收稿日期:  2015-01-28
  • 网络出版日期:  2015-03-31
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