RESOLUTION OF THE ENANTIOMERS OF SOME β-AMINO ALCOHOLS USING CHIRAL DERIVATIZATION AND REVERSED-PHASE LIQUID CHROMATOGRAPHY

A convenient and rapid procedure for enantiomeric resolution of β-amino alcohol drugs, such as oxprenolol, propafenone, timolol and phenylephrine, is described. The method is based on derivatization with the chiral reagent 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl isothiocyanate (GITC), and resolution of the resulting diastereomeric thioureas by reversed-phase HPLC using methanol-aqueous monobasic ammonium phosphate mixture as the mobile phase. The salt forms of these drugs can be directly derivatized with GITC reagent instead of being converted into their free bases and without protection of the phenolic hydroxyl group of phenylephrine.