Albendazole sulfoxide enantiomers: preparative chiral separation and absolute stereochemistry

Journal of Chromatography. a
Tiago C LourençoQ B Cass

Abstract

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.

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Citations

Dec 12, 2012·Antimicrobial Agents and Chemotherapy·Adriana ParedesUNKNOWN Cysticercosis Working Group in Peru
Apr 11, 2012·Journal of Pharmaceutical and Biomedical Analysis·Kátia Roberta A BelazRegina V Oliveira
Jun 15, 2016·Chirality·Tohru TaniguchiKenji Monde
Mar 3, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Joana TeixeiraCarla Fernandes
Apr 25, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Madalena M M PintoMaria E Tiritan
Jun 6, 2014·ACS Medicinal Chemistry Letters·Romain Stalder, Gregory P Roth

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