A Novel Method for Large-Scale Synthesis of Lamivudine through Cocrystal Formation of Racemic Lamivudine with (S)-(−)-1,1′-Bi(2-naphthol) [(S)-(BINOL)]

A large-scale synthesis of (−)-[2R,5S]-4-amino-1- [2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-2(1H)-pyrimidin-2-one (lamivudine) through resolution of racemic lamivudine by cocrystal formation with (S)- BINOL has been demonstrated. Lamivudine of very high purity with an enantiomeric excess of more than...

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Bibliographic Details
Published in:Organic process research & development 2009-05, Vol.13 (3), p.450-455
Main Authors: Roy, Bhairab Nath, Singh, Girij Pal, Srivastava, Dhananjai, Jadhav, Harishchandra S, Saini, Manmeet B, Aher, Umesh P
Format: Article
Language:English
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Summary:A large-scale synthesis of (−)-[2R,5S]-4-amino-1- [2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-2(1H)-pyrimidin-2-one (lamivudine) through resolution of racemic lamivudine by cocrystal formation with (S)- BINOL has been demonstrated. Lamivudine of very high purity with an enantiomeric excess of more than 99.9% was obtained. All four isomers of lamivudine have also been separated and characterized. Interestingly, cis-(−)- and trans-(−)-enantiomers form cocrystals with (S)-BINOL.
ISSN:1083-6160
1520-586X
DOI:10.1021/op800228h