Albendazole sulfoxide enantiomers: Preparative chiral separation and absolute stereochemistry

The enantiomeric separation of albendazole sulfoxide was carried out by simulated moving bed chromatography with variable zones (VARICOL). An overall recovery of 97% was achieved and enantiomeric ratios of 99.5% for raffinate and 99.0% for extract were attained. A total of 880 mg of (+)-albendazol sulfoxide and 930 mg of its antipode were collected after 55 cycles or 11 h of process, resulting in a mass rate of 2 g/day. Furthermore the absolute configuration of the enantiopure compounds was determined for the first time by vibrational circular dichroism (VCD) with the aid of theoretical calculations as (−)-(S) and (+)-(R)-albendazole sulfoxide.

► Isolation of albendazole sulfoxide enantiomers by VARICOL process.
► High purities of enantiomers were achieved with a 100% methanol as eluent.
► Solvent re-usage resulting in low discard volumes was an important achievement.
► (−)-(S) and (+)-(R)-albendazole sulfoxide determined by VCD and DFT calculations.