Tetrahydrofuran → (R)-4-(4-isopropyl-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 (127 mg, 0.382 mmol) (Y.-J. Shi et al., Tetrahedron, 1999, 55, 909-918) and triethylamine (0.053 mL, 0.382 mmol) were added to a solution of p-nitrophenylchloroformate (77 mg, 0.382 mmol) in tetrahydrofuran (45 mL) at 0° C. After 1 h, additional triethylamine was added (0.106 mL, 0.764 mmol) along with 4-isopropyl-1-piperidin-4-yl-1,3-dihydro-2H-imidazol-2-one (80 mg, 0.382 mmol). The reaction stirred at 0 oC for 10 min and was then heated to 50oC. After 2 h, the reaction was concentrated and redissolved in ethyl acetate. The organics were 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 100 mg of the titled compound. MS 569.24 (M+1).

Provenance & Evidence