Dimethyl Sulfoxide → HCID 468478, compound

Participants

Reaction Conditions

Reaction Steps

A solution of dimethyl sulfoxide (4.07 g, 52 mmol) and oxalyl chloride (3.61 g, 28 mmol) were added slowly in that order to dichloromethane (50 ml) at -78° C. (S)-[1-Benzyl-2-(3-hydroxy-pyrrolidin-1-yl)-2-oxo-ethyl]-carbamic acid tert-butyl ester (24 mmol) in dichloromethane (30 ml) was added to the above solution via canula, the reaction temperature brought to -30° C. for 0.5 hours, then lowered to -78° C. followed by the addition of triethylamine (118 mmol). The reaction was then warmed to 25° C., diluted with ethyl acetate, washed three times with 1:1 saturated NaHCO3 /brine, the organics dried over MgSO4 and concentrated. The resulting foam was purified by chromatography on silica gel eluted with 30, 40 and 50% ethyl acetate in hexanes to give a light yellow foam (7.5 g, 95% yield).

Provenance & Evidence