Dimethyl Sulfoxide → HCID 12073625, compound

Participants

Reaction Conditions

Reaction Steps

Oxalyl chloride (25 mL, 50 mmol) was dissolved in DCM (400 mL) and cooled to −78° C. under a nitrogen atmosphere, to which a solution consisting of DMSO (4.5 mL) in DCM (150 mL) was added. The reaction mixture was stirred for 15 minutes at −78° C. and a solution consisting of (Z)-isopropyl 7-((1R,2S,3S,5S)-3-fluoro-2-(hydroxymethyl)-5-(tetrahydro-2H-pyran-2-yloxy)cyclopentyl)hept-5-enoate (prepared in Step F, 12.94 g, 33.36 mmol) in DCM was subsequently added slowly. The reaction mixture was stirred for 40 minutes and triethylamine (28 mL) was subsequently added. Stirring was continued as the reaction mixture was allowed to warm to room temperature for 2 hours, monitoring by TLC. The reaction was acidified with 5% KHSO4, extracted with DCM, and the organic layers were washed twice with brine. After drying over sodium sulfate, filtration, and solvent removal under reduced pressure, the crude product was purified on silica gel, eluted with hexanes-ethyl acetate (85:15) to afford the title intermediate (10.31 g, 80%).

Provenance & Evidence