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THE DETERMINATION OF THE STEREOISOMERS OF A MULTIFUNCTIONAL B-ADRENOCEPTOR AGENT BY CHIRAL DERIVATIZATION AND HPLC

The reaction of chiral methylbenzyl and napthylethyl isocyanates with a β-adrenoceptor agent having two stereogenic centers and multiple reaction sites was investigated as a means of ascertaining the stereochemical composition of an individual enantiomer during chemical process development. The products of the reaction were unequivocally assigned using mass spectrometry (MS) and nuclear magnetic resonance (NMR). Both one and two equivalents of the isocyanate were found to add to the target analyte. Normal phase high-performance liquid chromatography using the chiral methylbenzyl isocyanate as the derivatizing reagent was found to give acceptable selectivity and sensitivity for the diastereomeric derivatives.