Naslov
Separation, Conformation in Solution and Absolute Configuration of Ethopropazine Enantiomers

Autori
Šinko, Goran ; Novak, Predrag ; Žiher, Dinko ; Vinković, Vladimir ; Šunjić, Vitomir ; Simeon-Rudolf, Vera

Izvornik
Enantiomer (1024-2430) 7 (2002), 2-3; 149-156

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
ethopropazine enantiomers; fractional crystallization; HPLC; chiral columns; NMR; CD; absolute configuration

Sažetak
Enantiomers of ethopropazine.HCl (10-(2-diethylaminopropyl) phenothiazine hydrochloride) were prepared by fractional crystallization of diastereomeric dibenzoyltartaric acid salts, and their optical purity (enantiomeric excess, ee) determined by HPLC on Chiralcel OJ column.With a solvent mixture n-hexane/t-butanol/triethylamine (100:3:0.5) as eluent a very good enantioseparation (alfa=1.68) for racemic ethopropazine was obtained. Enantiomeric purity for (-)-enantiomer was 99.1% and for (+)-enantiomer 97.9%. Combined data from NMR and CD spectra of both enantiomers, along with previously reported X-ray structure analyses of racemic ethopropazine, revealed skewed conformation of tricyclic system in solution, and (S)-configuration on the stereogenic center for (-)-enantiomer, and (R)-configuration for (+)- enantiomer.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

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