The chemical resolution of racemic cis-2-hydroxymethyl-5(cytosine-1 '-yl)-1,3-oxathiolane (BCH-189)-one direct method to obtain lamivudine as anti-HIV and anti-HBV agent

Racemic cis-BCH-189 can be resolved to (-)-enantiomer (lamivudine) and (+)-enantiomer by esterification of cis-2-hydroxymethyl-5-(N-4(')-acetylcytosine-1'-yl)-1,3-oxathiolane and (+)-menthyl chloroformate in CH3CN with pyridine as base. The two diastereomers of ester were seperated by recrystallization in methanol at 0degreesC. Lamivudine was obtained by deprotection of (-)-diastereomer with high yield.