Dimethyl Sulfoxide → HCID 67407708, compound

Participants

Reaction Conditions

Reaction Steps

A solution of DMSO (3.94 mL, 55.6 mmol) in dichloromethane (90 mL) at −78° C. was treated dropwise with oxalyl chloride (20.8 mL, 2 M in dichloromethane), stirred at −78° C. for 15 minutes, treated with a solution of the product from Example 115B (6.76 g, 27.8 mmol) in dichloromethane (230 mL) over 10 minutes, stirred at −78° C. for 20 minutes, treated dropwise with triethylamine (16.7 mL, 119.5 mmol) at −78° C., and after 10 minutes the reaction was warmed to 0° C., and stirred for an additional 10 minutes. The reaction mixture was quenched with water and partitioned between dichloromethane and water. The organic phase was washed with brine and dried over Na2SO4, filtered and concentrated. The residue was chromatographed on silica gel eluting with 5% ethyl acetate in chloroform to give the title compound (4.9 g, 73% yield).

Provenance & Evidence