Beilstein J. Org. Chem.2014,10, 3038–3055, doi:10.3762/bjoc.10.322
Pawel Borowiecki Daniel Paprocki Maciej Dranka Warsaw University of Technology, Faculty of Chemistry, Noakowskiego St. 3, 00-664 Warsaw, Poland 10.3762/bjoc.10.322 Abstract Enantioenriched promethazine and ethopropazine were synthesized through a simple and straightforward four-step
bromo derivative, which conducted in toluene gives mainly the product of single inversion, whereas carried out in methanol it provides exclusively the product of net retention. Enantiomeric excess of optically active promethazine and ethopropazine were established by HPLC measurements with chiral
columns.
Keywords: ethopropazine; lipase-catalyzed kinetic resolution; Mosher methodology; promethazine; stereodivergent synthesis; Introduction
Since enantiomorphs of biologically active compounds exhibit significant differences in their pharmacokinetic and pharmacodynamic behavior, optical purity of
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Graphical Abstract
Scheme 1:
Chemoenzymatic synthesis of enantioenriched enantiomers of promethazine 9 and ethopropazine 10. Rea...