2,2,2-Trifluoroethylamine hydrochloride → HCID 86593165, compound

Participants

Reaction Steps

1,1′-Thiocarbonyldiimidazole (0.980 g, 5.50 mmol, 1.2 equiv.) was dissolved in CH2Cl2 (200 mL), followed by addition of diisopropylethylamine (3.2 mL), and trifluoroethylamine hydrochloride (0.620 g, 4.58 mmol, 1.0 equiv.). The solution was stirred for 1 h at ambient temp, then 2-amino-N-[1-(benzoxazol-2-ylhydroxymethyl)-propyl]-3-phenylmethanesulfonylpropionamide was added in one portion. After stirring overnight, the reaction mixture was diluted with EtOAc (150 mL), washed with saturated bicarb, brine, dried over MgSO4. Purification with flash chromatography (50% ETOAc/hexanes as eluent) afforded N-[1-(benzoxazol-2-ylhydroxymethyl)-propyl]-3-phenylmethanesulfonyl-2-[3-(2,2,2-trifluoroethyl)thioureido]propionamide (0.720 g) as a mixture of diasteomers.

Provenance & Evidence