Dimethyl Sulfoxide → HCID 117761404, compound

Participants

Reaction Steps

To a solution of DMSO (0.04 mL, 0.62 mmol) in dry DCM (1.0 mL) under nitrogen atmosphere, was added oxalyl chloride (0.02 mL, 0.28 mmol) at −78° C. The reaction mixture was stirred at this temperature for 5 min followed by addition of a solution of (2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(4-cyano-3-(4-(2-hydroxyethoxy)benzyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate (140 mg, 0.24 mmol), in DCM (1 mL). The reaction mixture was stirred at −78° C. for 30 min followed by addition of triethylamine (0.16 mL, 1.20 mmol) and further stirring at same temperature for 10 min and then at r.t. for 10 min. The reaction mixture was diluted with hexane (50 mL) and filtered to remove the solids. The filterate was dried over Na2SO4 and concentrated in vacuo to afford crude title compound (100 mg, 72%) as viscous oil which was used without purification for the next step.

Provenance & Evidence