engleski

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

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)carbonylaminolpropan-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.

Chiral stationary phase (csp); 4-chloro-3; 5-dinitrobenzoic acid; 4-aryl-3; 4-dihydro-2(1h)-pyrimidones (dhpm)

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