High-performance liquid chromatographic enantioseparation of bicalutamide and its related compounds.
Direct high-performance liquid chromatographic methods were developed for the enantioseparation of (R,S)-bicalutamide (1) and its analogs (+/-)-3-chloro-N-(4-cyano-3-(trifluoromethyl)phenyl)-2-hydroxy-2-methylpropanamide (2), (+/-)-N-(4-cyano-3-(trifluoro-methyl)phenyl)-2-methyloxirane-2-carboxamide (3), (+/-)-4-fluorophenylsulfonyl-2-hydroxy-2-methylpropionic acid (4) and (+/-)-3-hydroxy-N-(4-cyano-3-(trifluoromethyl)phenyl)-2-hydroxy-2-methylpropanamide (5). The methods involved the use of a cellulose-based Chiralcel OD-H, macrocyclic glycopeptide-based Chirobiotic T, TAG and R, beta-cyclodextrin-based Cyclobond I 2000SN and t-butyl carbamate-derivatized quinine-based columns. The conditions affording the best resolution were found by selection and variation of the mobile-phase compositions, and the differences in separation capability of the methods were noted. The sequence of elution of the enantiomers was determined in all cases.
Török
Roland
R
Department of Inorganic and Analytical Chemistry, University of Szeged, Dóm tér 7, H-6720 Szeged, Hungary.
Bor
Adám
A
Orosz
György
G
Lukács
Ferenc
F
Armstrong
Daniel W
DW
Péter
Antal
A
D000813:Anilides / Q000737:chemistry / Q000302:isolation & purification*; D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000302:isolation & purification*; D002219:Carbamates / Q000737:chemistry; D002482:Cellulose / Q000737:chemistry; D002851:Chromatography, High Pressure Liquid / Q000379:methods*; D006020:Glycopeptides / Q000737:chemistry; D009570:Nitriles; D011803:Quinine / Q000737:chemistry; D012997:Solvents / Q000737:chemistry; D013237:Stereoisomerism; D013997:Time Factors; D014105:Tosyl Compounds
D000813:Anilides; D000900:Anti-Bacterial Agents; D002219:Carbamates; D006020:Glycopeptides; D009570:Nitriles; D012997:Solvents; D014105:Tosyl Compounds; D002482:Cellulose; C053541:bicalutamide; D011803:Quinine