1,2-Dichloroethane → [3-(1-methyl-2-oxo-1,2,3,5-tetrahydro-benzo[e][1,4]diazepin-4-yl)-3-oxo-(R)-1-(2,4,5-trifluoro-benzyl)-propyl]-carbamic acid tert-butyl ester

Participants

Reaction Steps

To a solution of (R)-3-[(tert-butoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid (80 mg, 0.24 mmol) in dry DCM (10 mL), was added HOBT (42 mg, 0.31 mmol), EDC (59 mg, 0.31 mmol) and DIPEA (0.20 mL, 1.2 mmol). The reaction mixture was stirred at r.t. for 10 min. A solution of 1-methyl-1,3,4,5-tetrahydrobenzo (e) [1,4]diazepin-2-one trifluoroacete (70 mg, 0.24 mmol) in dry DCM (5 mL) was added and the reaction mixture was stirred at r.t. overnight. After the completion of the reaction, as confirmed by TLC, the crude product was extracted with DCM (10 mL) and washed sequentially with 10%. HCl solution (10 mL) and saturated solution of sodium bicarbonate (10 mL). The organic layer was separated and washed with brine and dried over Na2SO4. The solvents were removed in vacuo to afford the crude compound, which was purified by column chromatography (silica gel, 3:7 EtOAc:Pet.Ether) to afford 2 [3-(1-methyl-2-oxo-1,2,3,5-tetrahydro-benzo[e][1,4]diazepin-4-yl)-3-oxo-(R)-1-(2,4,5-trifluoro-benzyl)-propyl]-carbamic acid tert-butyl ester (95 mg, 78%) as viscous oil.

Provenance & Evidence