Tetrahydrofuran → (R)-4-(2-oxo-2,3-dihydroimidazol-1-yl)-N-(2-oxo-5-phenyl-1-(2,2,2-trifluoroethyl)-2,3-dihydro-1H-benzo[e][1,4]diazepin-3-yl)piperidine-1-carboxamide

Participants

Reaction Steps

(3R)-3-Amino-5-phenyl-1-(2,2,2-trifluoroethyl) 1,3-dihydro-2H-1,4-benzodiazepin-2-one (199 mg, 0.598 mmol) (Y.-J. Shi et al., Tetrahedron, 1999, 55, 909-918) and triethylamine (83 uL, 0.598 mmol) in tetrahydrofuran (5 mL) were added to a solution of p-nitrophenylchloroformate (100 mg, 0.598 mmol) in tetrahydrofuran (15 mL) at 0 oC. After 1 h, 1-piperidin-4-yl-1,3-dihydro-2H-imidazol-2-one (100 mg, 0.598 mmol) in tetrahydrofuran (9 mL) and dimethylforamide (1 mL) were added and stirred at 0 oC for 10 min and then warned to room temperature. After 16 h, the reaction was concentrated and the residue dissolved in ethyl acetate, washed with 1 N sodium hydroxide solution (3×), water, brine, and dried over magnesium sulfate. Purification by silica gel chromatography (100% dichloromethane→10% methanol/dichloromethane) gave 70 mg of the titled compound. MS 527.5 (M+1).

Provenance & Evidence