Patent ID: 8318933
Filing Date: 2012-11-27
Classification: C07D

Abstract:
1. A process to prepare (3S)-5-[4-(4-fluorophenyl)-6-isopropyl-2-(N-methyl-N-methylsulfonylamino)pyrimidin-5-yl]-3-hydroxy-(4E)-pentenoic acid of Formula V, wherein R a) reacting (2E)-3-[4-(4-fluorophenyl)-6-isopropyl-2-(N-methyl-N-methanesulfonylamino)pyrimidine]-propenal of Formula II, with a compound of Formula III a or III b wherein R′, R″ and R′″ represent alkyl, aralkyl, cycloalkyl, substituted cycloalkyl, phenyl, substituted phenyl, naphthyl, substituted naphthyl or heterocyclic residue, in the presence of a base selected from the group consisting of n-butyllithium, lithium hexamethyldisilazane, sodium hexamethyldisilazane and lithium diisopropylamine and an organic solvent, in the absence of MgBr wherein R′, R″ and R′″ are defined as above, b) hydrolyzing the mixture of compounds of Formula IVa or IVb to its corresponding acid obtaining a mixture of compounds of Formula X isomers c) purifying compounds of Formula X by using optically pure precipitating agents in a mixture of organic solvent and water to get enantiomerically pure compound of Formula XI; and d) esterifying the compound of Formula XI to get enantiomerically pure compound of Formula V.