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Enantioseparation of racemic 4-aryl-3,4-dihydro-2(1H)-pyrimidones on chiral stationary phases based on 3,5-dimethylanilides of N-(4-alkylamino-3,5-dinitro)benzoyl L-α-amino acids

✍ Scribed by Darko Kontrec; Vladimir Vinković; Vitomir Šunjić; Birgit Schuiki; Walter M.F. Fabian; C. Oliver Kappe

Publisher
John Wiley and Sons
Year
2003
Tongue
English
Weight
178 KB
Volume
15
Category
Article
ISSN
0899-0042

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✦ Synopsis

Abstract

Three novel chiral packing materials for high‐performance liquid chromatography were prepared by covalently binding of (2S)‐N‐(3,5‐dimethylphenyl)‐2‐[(4‐chloro‐3,5‐dinitrophenyl)carbonylamino]propan‐amide (7), (2S)‐N‐(3,5‐dimethylphenyl)‐2‐[(4‐chloro‐3,5‐dinitrophenyl)carbonylamino]‐4‐methylpentanamide (8), and (2S)‐N‐(3,5‐dimethylphenyl)‐2‐[(4‐chloro‐3,5‐dinitrophenyl)carbonyl‐amino]‐2‐phenylacetamide (9) to aminopropyl silica. The resulting chiral stationary phases (CSPs 1–3) proved effective for the resolution of racemic 4‐aryl‐3,4‐dihydro‐2(1H)‐pyrimidone derivatives (TR 1–14). The mechanism of their enantioselection, supported by the elution order of (S)‐TR 13 and (R)‐TR 13 and molecular modeling of the complex of the slower running (S)‐TR 13 with CSP 1 is discussed. Chirality 15:550–557, 2003. © 2003 Wiley‐Liss, Inc.

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