Ethylmorpholine → L-Isoleucine

Participants

Reaction Conditions

Reaction Steps

A -5° C. solution of L-isoleucine, N-[1-(carboxymethyl)-L-prolyl] benzylamide (202 mg, 0.53 mmol, 1.0 eq), N-ethylmorpholine (82 uL, 0.64 mmol, 1.20 eq) in acetonitrile (8 mL) was treated with isobutyl chloroformate (80 uL, 0.62 mmol, 1.15 eq) followed by 2-methylpiperidine (0.106 g, 1.07 mmol, 2.0 eq). The solution was warmed to 22° C., concentrated to a residue, and purified by flash chromatography to provide 80 mg (32%) of L-isoleucine, N-[1-[2-(N-(2-methylpiperidine))-2-oxoethyl]-L-prolyl] benzylamide as a colorless oil.

Provenance & Evidence