Dimethyl Sulfoxide → HCID 53952975, compound

Participants

Reaction Steps

To a well-stirred dry ice/acetone bath chilled solution of oxalyl chloride (163,μl, 1.91 mmol) in methylene chloride (4.5 ml), a solution of dimethyl sulfoxide (259 μl, 3.6 mmol) in methylene chloride (2.25 ml) was added dropwise while maintaining the temperature below -55° C. After stirring the reaction at that temperature for 5 minutes, N-adamantan-1-yl-2-hydroxymethyl-3-pyridin-4-yl-2-pyridin-4-ylmethyl-propion-amide (700 mg, 1.73 mmol) in methylene chloride (2.25 ml) was added, and the reaction was stirred for 30 minutes. Triethylamine (1.20 ml, 8.65 mmol) was added, and the reaction was stirred for 5 minutes before removing the cooling bath. After stirring for 20 minutes at ambient temperature, the reaction was quenched by addition to water/methylene chloride (40 ml of each). The mixture was then extracted three times with 40 ml portions of methylene chloride. The combined extracts were dried (anhydrous sodium sulfate) and concentrated in vacuo to afford a yellow oil (1.14 g). Flash chromatography of the entire sample (silica gel, 40 micron mesh; elution initially with methanol/methylene chloride=3:97 in volume, and increasing the methanol concentration during elution finally to methanol/methylene chloride=1:9 in volume) afforded the title compound (475 mg) as an oil.

Provenance & Evidence