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

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

Journal of chromatography. A (2005-11-30)
Roland Török, Adám Bor, György Orosz, Ferenc Lukács, Daniel W Armstrong, Antal Péter
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, 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.

MATERIALS
Product Number
Brand
Product Description

Supelco
Astec® CYCLOBOND I 2000 Chiral HPLC Column, 5 μm particle size, L × I.D. 25 cm × 4.6 mm
Supelco
Astec® CYCLOBOND I 2000 Chiral HPLC Column, 5 μm particle size, L × I.D. 15 cm × 2.1 mm
Supelco
Astec® CYCLOBOND I 2000 Chiral HPLC Column, 5 μm particle size, L × I.D. 25 cm × 10 mm
Supelco
Astec® CYCLOBOND I 2000 Chiral HPLC Column, 5 μm particle size, L × I.D. 10 cm × 2.1 mm
Supelco
Astec® CHIROBIOTIC® V Chiral HPLC Column, 5 μm particle size, L × I.D. 10 cm × 2.1 mm
Supelco
Astec® CHIROBIOTIC® T Chiral HPLC Column, 5 μm particle size, L × I.D. 10 cm × 4.6 mm
Supelco
Astec® CYCLOBOND I 2000 HP-RSP Chiral HPLC Column, 5 μm particle size, L × I.D. 25 cm × 4.6 mm
Supelco
Astec® CHIROBIOTIC® TAG Chiral HPLC Column, 5 μm particle size, L × I.D. 25 cm × 10 mm
Supelco
Astec® CHIROBIOTIC® T Chiral HPLC Column, 5 μm particle size, L × I.D. 25 cm × 2.1 mm
Supelco
Astec® CYCLOBOND I 2000 HP-RSP Chiral HPLC Column, 5 μm particle size, L × I.D. 15 cm × 4.6 mm
Supelco
Astec® CHIROBIOTIC® T Chiral HPLC Column, 5 μm particle size, L × I.D. 15 cm × 2.1 mm
Supelco
Astec® CHIROBIOTIC® TAG Chiral HPLC Column, 5 μm particle size, L × I.D. 10 cm × 4.6 mm
Supelco
Astec® CHIROBIOTIC® T Chiral HPLC Column, 5 μm particle size, L × I.D. 25 cm × 4.6 mm
Supelco
Astec® CHIROBIOTIC® TAG Chiral HPLC Column, 5 μm particle size, L × I.D. 15 cm × 4.6 mm
Supelco
Astec® CHIROBIOTIC® T Chiral HPLC Column, 5 μm particle size, L × I.D. 25 cm × 10 mm
Supelco
Astec® CHIROBIOTIC® V Chiral HPLC Column, 5 μm particle size, L × I.D. 25 cm × 4.6 mm
Supelco
Astec® CHIROBIOTIC® T Chiral HPLC Column, 5 μm particle size, L × I.D. 10 cm × 3 mm
Supelco
Astec® CHIROBIOTIC® R Chiral HPLC Column, 5 μm particle size, L × I.D. 25 cm × 4.6 mm
Supelco
Astec® CHIROBIOTIC® TAG Chiral HPLC Column, 5 μm particle size, L × I.D. 10 cm × 2.1 mm
Supelco
Astec® CHIROBIOTIC® V Chiral HPLC Column, 5 μm particle size, L × I.D. 25 cm × 21.2 mm
Supelco
Astec® CHIROBIOTIC® T Chiral HPLC Column, 5 μm particle size, L × I.D. 10 cm × 2.1 mm
Supelco
Astec® CHIROBIOTIC® V Chiral HPLC Column, 5 μm particle size, L × I.D. 15 cm × 4.6 mm
Supelco
Astec® CHIROBIOTIC® R Chiral HPLC Column, 5 μm particle size, L × I.D. 25 cm × 2.1 mm
Supelco
Astec® CHIROBIOTIC® TAG Chiral HPLC Column, 5 μm particle size, L × I.D. 25 cm × 2.1 mm
Supelco
Astec® CHIROBIOTIC® V Chiral HPLC Column, 5 μm particle size, L × I.D. 15 cm × 2.1 mm
Supelco
Astec® CHIROBIOTIC® R Chiral HPLC Column, 5 μm particle size, L × I.D. 15 cm × 2.1 mm
Supelco
Astec® CHIROBIOTIC® T Chiral HPLC Column, 5 μm particle size, L × I.D. 15 cm × 4.6 mm
Supelco
Astec® CHIROBIOTIC® R Chiral HPLC Column, 5 μm particle size, L × I.D. 15 cm × 4.6 mm
Supelco
Astec® CHIROBIOTIC® TAG Chiral HPLC Column, 5 μm particle size, L × I.D. 25 cm × 4.6 mm
Supelco
Astec® CHIROBIOTIC® V Chiral HPLC Column, 5 μm particle size, L × I.D. 10 cm × 4.6 mm