Dicyclohexylcarbodiimide → HCID 67616063, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of N-t-butoxycarbonyl-L-tryptophan, (128 g, 0.42 mol), 2-(2-aminoethoxy)ethanol (46.42 g, 0.44 mol), 1-hydroxybenzotriazole (60.0 g, 0.44 mol) in 700 mL of DMF at 0° C. was added DCC (100 g, 0.48 mol). After stirring at 0° C. for 15 minutes, the mixture was stirred at room temperature overnight. The white solids were filtered and washed with EtOAc. The filtrate was concentrated under reduced pressure. The residue was taken up in ether and a small amount of EtOAc, washed with it HCl (3×500 mL), saturated NaHCO3 (3×500 mL), and brine (3×500 mL). The organic layer was dried (MgSO4), filtered and concentrated to give 2-(S)-t-butoxycarbonylamino-N-[2-(2-hydroxy-ethoxy)ethyl]-3-(1H-indol-3-yl)-propionamide, 150 g (yield 91%), MS: 392.2 (M+H)+.

Provenance & Evidence