High-performance liquid chromatographic enantioseparation of bicalutamide and its related compounds

Roland Török, Ádám Bor, G. Orosz, Ferenc Lukács, Daniel W. Armstrong, A. Péter

Research output: Contribution to journalArticle

17 Citations (Scopus)

Abstract

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, β-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.

Original languageEnglish
Pages (from-to)75-81
Number of pages7
JournalJournal of Chromatography A
Volume1098
Issue number1-2
DOIs
Publication statusPublished - Dec 9 2005

Fingerprint

Isobutyrates
Quinine
Carbamates
Enantiomers
Glycopeptides
Cyclodextrins
Phase composition
Cellulose
Liquids
propylene oxide
bicalutamide
chirobiotic T
cellulose tris-3,5-dimethylphenyl-carbamate

Keywords

  • Bicalutamide
  • Cellulose-tris-3,5-dimethylphenyl carbamate-based stationary phase
  • Chiralcel OD-H
  • Chirobiotic phases
  • Direct enantiomeric separation
  • High-performance liquid chromatography
  • Macrocyclic glycopeptide type stationary phases

ASJC Scopus subject areas

  • Analytical Chemistry

Cite this

High-performance liquid chromatographic enantioseparation of bicalutamide and its related compounds. / Török, Roland; Bor, Ádám; Orosz, G.; Lukács, Ferenc; Armstrong, Daniel W.; Péter, A.

In: Journal of Chromatography A, Vol. 1098, No. 1-2, 09.12.2005, p. 75-81.

Research output: Contribution to journalArticle

Török, Roland ; Bor, Ádám ; Orosz, G. ; Lukács, Ferenc ; Armstrong, Daniel W. ; Péter, A. / High-performance liquid chromatographic enantioseparation of bicalutamide and its related compounds. In: Journal of Chromatography A. 2005 ; Vol. 1098, No. 1-2. pp. 75-81.
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