Triethylamine → L-isoleucine, N-[1-(adamantan-2-ylcarbamoylmethyl)-L-prolyl] benzylamide

Participants

Reaction Steps

Using the procedure described previously, a solution of L-isoleucine, N-[1-(carboxymethyl)-L-prolyl] benzylamide (113 mg, 0.30 mmol), triethylamine (168 uL, 1.20 mmol, 4 eq) in acetonitrile (1.5 mL, was cooled to 0° C. and treated with isobutyl chloroformate (43 uL, 0.33 mmol, 1.1 eq) followed by the hydrochloride salt of 2-adamantylamine (113.2 mg, 0.60 mmol, 2 eq). After TLC indicated the reaction was complete, the mixture was purified by HPLC to provide 10 mg (6.5%) of L-isoleucine, N-[1-(adamantan-2-ylcarbamoylmethyl)-L-prolyl] benzylamide.

Provenance & Evidence