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Liquid chromatographic resolution of 3‐amino‐1,4‐benzodiazepin‐2‐ones on crown ether‐based chiral stationary phases
Author(s) -
Park Je Young,
Jin Kab Bong,
Hyun Myung Ho
Publication year - 2012
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.22041
Subject(s) - chemistry , silanol , crown ether , ammonium acetate , chromatography , alcohol , resolution (logic) , chirality (physics) , perchloric acid , amino acid , aqueous solution , organic chemistry , high performance liquid chromatography , catalysis , physics , quantum mechanics , ion , biochemistry , chiral symmetry breaking , artificial intelligence , computer science , nambu–jona lasinio model , quark
3‐Amino‐5‐phenyl (or 5‐methyl)‐1,4‐benzodiazepin‐2‐ones, which are chiral precursors of anti‐respiratory syncytial virus active agents, were resolved on three different chiral stationary phases (CSPs) based on (+)‐(18‐crown‐6)‐2,3,11,12‐tetracarboxylic acid or (3,3′‐diphenyl‐1,1′‐binaphthyl)‐20‐crown‐6. Among the three CSPs, the CSP that is based on (3,3′‐diphenyl‐1,1′‐binaphthyl)‐20‐crown‐6 and containing residual silanol group‐protecting n ‐octyl groups on the silica surface was found to be most effective with the use of 80% ethanol in water containing perchloric acid (10 mM) and ammonium acetate (1.0 mM) as a mobile phase. The separation factors (α) and resolutions (R S ) were in the range of 1.90–3.21 and 2.79–5.96, respectively. From the relationship between the analyte structure and the chromatographic resolution behavior, the chiral recognition mechanism on the CSP based on (+)‐(18‐crown‐6)‐2,3,11,12‐tetracarboxylic acid was proposed to be different from that on the CSP based on (3,3′‐diphenyl‐1,1′‐binaphthyl)‐20‐crown‐6. In addition, the chromatographic resolution behavior of the most effective CSP was investigated as a function of the composition of aqueous mobile phase containing organic and acidic modifier and ammonium acetate. Chirality 24:427‐431, 2012 . © 2012 Wiley Periodicals, Inc.