Dimethyl Sulfoxide → HCID 89442768, compound

Participants

Reaction Steps

Oxalyl chloride (0.042 mL, 0.51 mmol) was added to a solution of DMSO (0.071 mL, 1.01 mmol) in dry DCM (0.5 mL) at −78° C. under nitrogen atmosphere. The reaction mixture was stirred for 5 min. at the same temperature and then a solution of (2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(4-chloro-3-(4-(2-hydroxyethoxy)benzyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate (150 mg, 0.25 mmol), in dry DCM (2 mL) was added. The reaction mixture was stirred at the same temperature for 1 h. NEt3 (0.211 mL, 1.518 mmol) was added and the reaction mixture was allowed to come to r.t. The crude compound was extracted with DCM (20 mL). The organic layer was separated, washed with water (15 mL). The combined organic layers were dried over Na2SO4 and concentrated in vacuo to afford the title compound which was used as such in next step.

Provenance & Evidence