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Separation, Conformation in Solution and Absolute Configuration of Ethopropazine Enantiomers

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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 (α = 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.
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Keywords: CD; HPLC; NMR; absolute configuration; chiral columns; ethopropazine enantiomers; fractional crystallization

Document Type: Research Article

Affiliations: 1: Institute for Medical Research and Occupational Health, Zagreb, Croatia 2: Pliva Pharm. Ind. Inc. Research Division, Prilaz baruna Filipovića 25, Zagreb, Croatia 3: Institute Ruđer Bošković, Bijenička cesta 54; Zagreb, Croatia

Publication date: March 1, 2002

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