title: Liquid chromatographic resolution of 3-amino-1,4-benzodiazepin-2-ones on crown ether-based chiral stationary phases.
abstract: 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.
authors.affiliation: Department of Chemistry and Chemistry Institute for Functional Materials, Pusan National University, Busan 609-735, Korea.
authors.forename: Je Young
authors.initials: JY
authors.lastname: Park
authors.forename: Kab Bong
authors.initials: KB
authors.lastname: Jin
authors.forename: Myung Ho
authors.initials: MH
authors.lastname: Hyun
mesh_terms: D000085:Acetates / Q000737:chemistry; D001569:Benzodiazepines / Q000737:chemistry*; D002853:Chromatography, Liquid / Q000379:methods*; D043844:Crown Ethers / Q000737:chemistry*; D015394:Molecular Structure; D012821:Silanes / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000085:Acetates; D043844:Crown Ethers; D012821:Silanes; C082343:silanol; C090732:18-crown-6 2,3,11,12-tetracarboxylic acid; D001569:Benzodiazepines; C096527:binaphthyl-20-crown-6; C018824:ammonium acetate