Tetrahydrofuran → HCID 11685917, compound

Participants

Reaction Steps

(3R)-3-Amino-5-phenyl-1-(2,2,2-trifluoroethyl)-1,3-dihydro-2H-1,4-benzodiazepin-2-one (23 mg, 0.069 mmol) (Y.-J. Shi et al., Tetrahedron, 1999, 55, 909-918) and triethylamine (0.009 μL, 0.069 mmol) were added to a solution of p-nitrophenylchloroformate (14 mg, 0.069 mmol) in tetrahydrofuran (15 mL) at 0 oC. After 1 h, 4-benzyl-1-piperidin-4-ylimidazolidin-2-one (18 mg, 0.069 mmol) and additional triethylamine (0.027 mL, 0.207 mmol) were added and the reaction warmed to ambient temperature. After 16 h, the reaction was concentrated and partitioned between ethyl acetate and 1 N sodium hydroxide solution. The organics were washed with water, brine, and dried over magnesium sulfate. Purification by silica gel chromatography (100% dichloromethane=9% methanol {1% ammonium hydroxide}/dichloromethane) gave the title compound (30 mg). MS 619.6 (M+1)

Provenance & Evidence