2,6-Lutidine → HCID 86627641, compound

Participants

Reaction Conditions

Reaction Steps

To a cold (−78° C.) mixture of trifluoromethanesulfonic anhydride (0.284 mL, 1.681 mmol), 2,6-lutidine (0.261 mL, 2.241 mmol) and CH2Cl2 (1 mL) was added (4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-[(3-hydroxypyrazin-2-yl)methyl]-4-methyl-1,3-oxazolidin-2-one (472 mg, 1.120 mmol) in CH2Cl2 (1 mL). The resulting mixture was stirred at −78° C. for 30 min then the cold bath was switched to an ice bath. Reaction mixture was stirred cold (0° C.) for additional 2 h. Crude mixture was worked up with water/CH2Cl2/Na2SO4/filtration/concentration to afford an orange oil. This was purified by preparative TLC (silica gel) developed with a EtOAc (30% v/v)/hexanes mixture to give a yellow oil as the titled compound. LCMS calc.=553.04; found=554.02 (M+H)+.

Provenance & Evidence