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Enantioseparation of racemic 4‐aryl‐3,4‐dihydro‐2(1 H )‐pyrimidones on chiral stationary phases based on 3,5‐dimethylanilides of N ‐(4‐alkylamino‐3,5‐dinitro)benzoyl L‐α‐amino acids
Author(s) -
Kontrec Darko,
Vinković Vladimir,
Šunjić Vitomir,
Schuiki Birgit,
Fabian Walter M.F.,
Kappe C. Oliver
Publication year - 2003
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.10200
Subject(s) - chemistry , dinitrophenyl , elution , aryl , covalent bond , chiral derivatizing agent , amide , high performance liquid chromatography , amino acid , enantiomer , stereochemistry , medicinal chemistry , organic chemistry , chiral column chromatography , chromatography , biochemistry , alkyl , antibody , immunology , biology
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.