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• W3008889733 abstract "Bedaquiline (BDQ) is the most critical pharmaceutical in the world for treating multidrug-resistant Mycobacterium tuberculosis. Despite it being highly effective, BDQ asymmetric synthesis remains a challenge. Herein, the influence of chiral bases, namely, bis(1-phenylethyl)amine, bisoxazoline, and sparteine on the diastereoselective lithiation reaction to obtain BDQ was investigated. The highest diastereoselective ratio (dr) emerged as 90:10 from the (+)-bis[(R)-1-phenylethyl] lithium amide. This is a significant improvement from the 50:50 dr achieved from the commercial synthesis. Thereafter, the desired (90:10 RS, SR) diastereomeric mixture was easily isolated via a gravity column and subjected to chiral supercritical fluid chromatography (SFC) to access the desired enantiomer (1R, 2S)-BDQ. The advantages of this procedure are enhanced diastereoselection as well as a greener, faster way to achieve excellent enantioseparation (up to 1.0 g scale)." @default.
• W3008889733 created "2020-03-06" @default.
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• W3008889733 date "2020-02-17" @default.
• W3008889733 modified "2023-10-17" @default.
• W3008889733 title "Improved Synthesis and Isolation of Bedaquiline" @default.
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• W3008889733 doi "https://doi.org/10.1021/acsomega.9b04037" @default.
• W3008889733 hasPubMedCentralId "https://www.ncbi.nlm.nih.gov/pmc/articles/7045498" @default.
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