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 C_sp3-C_sp3 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 C_sp3-C_sp3 bond cleavage

1.
Department of New Drug Research and Development, Institute of Materia Medica, Chinese Academy of Medical Sciences & Peking Union Medical College, Beijing 100050, China

Corresponding author: Ye Huang, Wen-Hua Feng,
Received Date: 28 January 2015
Available Online: 31 March 2015
Fund Project:

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 C_sp3-C_sp3 bond cleavage of a benzyl alcohol intermediate. And the precise conditions and mechanism of the base-catalyzed cleavage reaction were discussed.
- Bedaquiline,
- Inactive stereoisomers,
- Recycle,
- C_sp3-C_sp3 cleavage
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