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Liquid chromatographic resolution of 3‐amino‐1,4‐benzodiazepin‐2‐one derivatives on various Pirkle‐type chiral stationary phases
Author(s) -
Park Je Young,
Cho Hwan Sun,
Hyun Myung Ho
Publication year - 2011
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.20944
Subject(s) - chemistry , enantiomer , amide , chromatography , chiral derivatizing agent , chiral column chromatography , alcohol , stereochemistry , organic chemistry
Abstract The two enantiomers of N ‐acyl amide and N ‐ureide derivatives of 3‐amino‐5‐phenyl‐1,4‐benzodiazepin‐2‐ones, which have been known to show anti‐respiratory syncytial virus (RSV) activity, were resolved on seven different Pirkle‐type chiral stationary phases (CSPs) with the use of 10% isopropyl alcohol in hexane as a mobile phase. Among the seven Pirkle‐type CSPs, the one based on ( S )‐leucine derivative named as N ‐Phe‐ L ‐Leu was found to be most successful, the separation factors (α) and the resolutions ( R S ) for seven analytes being in the range of 1.78–4.21 and 5.94–15.08, respectively. By resolving N ‐benzyloxycarbonyl derivatives of 3‐amino‐5‐phenyl(or 5‐methyl)‐1,4‐benzodiazepin‐2‐ones on Pirkle‐type CSPs, the phenyl ring at the 5‐position and the NH hydrogen at the 1‐position of analytes were found to play an important role in the chiral recognition . Chirality, 2011. © 2011 Wiley Periodicals, Inc.