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-alpha-amino acids.
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.
Kontrec
Darko
D
Ruder Bosković Institute, Zagreb, Croatia.
Vinković
Vladimir
V
Sunjić
Vitomir
V
Schuiki
Birgit
B
Fabian
Walter M F
WM
Kappe
C Oliver
CO
D000596:Amino Acids / Q000138:chemical synthesis / Q000737:chemistry* / Q000302:isolation & purification; D000813:Anilides / Q000138:chemical synthesis / Q000737:chemistry* / Q000302:isolation & purification; D001565:Benzoates / Q000138:chemical synthesis / Q000737:chemistry* / Q000302:isolation & purification; D007202:Indicators and Reagents; D008958:Models, Molecular; D008968:Molecular Conformation; D011744:Pyrimidinones / Q000138:chemical synthesis / Q000737:chemistry* / Q000302:isolation & purification; D013237:Stereoisomerism
D000596:Amino Acids; D000813:Anilides; D001565:Benzoates; D007202:Indicators and Reagents; D011744:Pyrimidinones