Abstract
An efficient and concise approach for recognizing chirality and determining the absolute configuration of the diastereomers of (RS)-Betaxolol, [(RS)-Bet] is described, which in turn is a measure of the enantiomeric purity of Bet since the diastereomers were separated and isolated using preparative TLC. A reverse phase HPLC method was developed and validated for the enantioseparation of (RS)-Betaxolol. Diastereomers were synthesized, using a naproxen based chiral derivatizing reagent, under microwave irradiation. The absolute configuration of both diastereomers was established with the help of 1H NMR spectroscopy and by developing the lowest energy optimized structures of the diastereomers based on density functional theory. The configuration of the diastereomers was established as [(S)-Nap-(R)-Bet] and [(S)-Nap-(S)-Bet]. The determination of the absolute configuration of the two diastereomers lent support to elution order and separation mechanism. The limits of quantitation were found to be 0.80ngmL−1 for the diastereomers.
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