Dimethyl Sulfoxide → HCID 121362282, compound

Participants

Reaction Steps

DMSO (503 μL, 7.09 mmol) was added to a dry ice/acetone cooled solution of oxalyl chloride (253 μL, 2.84 mmol) in methylene chloride (5.0 mL). After 2 min, a solution of tert-butyl[(2R,3S)-2-(2,5-difluorophenyl)-5-hydroxytetrahydro-2H-thiopyran-3-yl]carbamate (490 mg, 1.42 mmol) in methylene chloride (5.0 mL) was added and the mixture was stirred for 30 min. Triethylamine (1.98 mL, 14.2 mmol) was added and the solution was stirred for 10 min and then removed from the dry ice/acetone bath and warmed to room temperature. Methylene chloride (50 mL) and water (30 mL) were added and the organic phase was dried with sodium sulfate, filtered and evaporated to an oil. The residue was placed onto preparative tlc plates, developed with 1:2 EtOAc/hexanes and eluted with EtOAc to give the title compound as a solid. The mixture was resolved by preparative HPLC Chiralpak AD chromatography eluting with 25% IPA/heptane to give the first eluting isomer, namely, tert-butyl[(2S,3R)-2-(2,5-difluorophenyl)-5-oxotetrahydro-2H-thiopyran-3-yl]carbamate and the second eluting title compound isomer, namely, tert-butyl[(2R,3S)-2-(2,5-difluorophenyl)-5-oxotetrahydro-2H-thiopyran-3-yl]carbamate.

Provenance & Evidence