Dicyclohexylcarbodiimide → HCID 178427592, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of Boc-D-Arg(Tos)OH (11.2 g, 26.1 mmol), HOBt (3.9 g, 28.7 g), glycine benzyl ester hydrochloride (5.2 g, 26.1 mmol) in 52 mL of DCM is added DIEA (4.5 mL, 26.1 mmol) followed by DCC (5.9 g, 28.7 mmol; dissolved in 5 mL of DCM). After stirring for 18 h, the reaction mixture is cooled to −10° C. and the precipitate is filtered off. The filtrate is extracted twice with 1N Hcl (50 mL), twice with 5% NaHCO3 (50 mL), brine (50 mL), dried (MgSO4), and concentrated in vacuo to give 15.2 g (100%) of Boc-D-Arg(Tos)Gly-Gly-OBn as a white solid. RP-HPLC: 18.9 min.;C18, 0-100% CH3CN over 25 min., 1.5 mL/min.

Provenance & Evidence