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Herstellung, optische Reinheit und Konfiguration der Flecainid‐Enantiomeren
Author(s) -
Blaschke Gottfried,
Scheidemantel Ursula,
Walther Bernd
Publication year - 1985
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19851181132
Subject(s) - chemistry , diastereomer , enantiomer , mandelic acid , absolute configuration , derivatization , stereochemistry , silica gel , enantiomeric excess , isocyanate , high performance liquid chromatography , chromatography , organic chemistry , enantioselective synthesis , catalysis , polyurethane
Preparation, Optical Purity and Configuration of the Enantiomers of Flecainide The chiral antiarrhythmic drug flecainide ( rac ‐ 1 ) was resolved by fractional crystallization of the diastereomeric salts with optically active mandelic acid. Derivatization with (+)‐1‐phenylethyl isocyanate and analytical separation of the diastereomers 3 by HPLC on silica gel confirmed the optical purity of the enantiomers. CD‐Spectra of the N ‐chloro derivatives established the absolute configuration: (−)‐ 1 is R ‐, (+)‐ 1 S ‐configurated.