Triethylamine → L-Isoleucine

Participants

Reaction Steps

A -5° C. solution of L-isoleucine, N-[1-(carboxymethyl)-L-prolyl] benzylamide (0.212 g, 0.56 mmol, 1.0 eq), and triethylamine (96 uL, 65 mg, 0.65 mmol, 1.15 eq), in acetonitrile (10 mL) was treated with isobutyl chloroformate (77 uL, 80 mg, 0.59 mmol, 1.05 eq) followed by pyrrolidine (94 uL, 80 mg, 1.13 mmol, 2.0 eq). Workup as above provided 205 mg (85%) of L-isoleucine, N-[1-[2-(1-pyrrolidine)-2-oxoethyl]-L-prolyl] benzylamide.

Provenance & Evidence