tert-Butanol → (S)-4-Dibenzofuran-2-yl-4-oxo-2-(2,2,2-trifluoro-acetylamino)-butyric acid tert-butyl ester

Participants

Reaction Conditions

Reaction Steps

To a DMF solution (10 mL) of (S)-4-dibenzofuran-2-yl-4-oxo-2-(2,2,2-trifluoroacetylamino)-butyric acid (0.3 g, 0.00079 mol) at 40° C. was added carbonyldimidazole (0.13 g, 0.00079 mol). This mixture was stirred for 1 hour and then 1,8-diazabicyclo-[5.4.0]undec-7-ene (DBU, 0.12 mL, 0.00079 mol) and t-butanol (0.15 mL, 0.00158 mol) were added. The reaction mixture was stirred for 24 hours at 40° C., cooled to 24° C., and then diluted with ether (20 mL). The solution was washed with water (2×10 mL), brine (2×10 mL), and dried over anhydrous magnesium sulfate. The mixture was filtered and the filtrate was concentrated to an oil by evaporation of the solvent in vacuo. The oil was flash chromatographed on silica gel eluting with 20% ethyl acetate/hexane (v/v) to yield the title compound; mp 92-94° C.

Provenance & Evidence