Albendazole sulfoxide enantiomers: Preparative chiral separation and absolute stereochemistry
- Lourenco, TC
- Batista, JM
- Furlan, M
- He, YA
- Nafie, LA
- Santana, CC
- Cass, QB
DOIAbstract
Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)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...