Triethylamine → N1-(4-(2-aminocyclopropyl)phenyl)-N8-hydroxyoctanediamide hydrochloride

Participants

Reaction Steps

Ethyl chloroformate (0.384 mmol, 0.04 mL) and triethylamine (0.42 mmol, 0.06 mL) were added to a cooled (0° C.) solution of 8-(4-(2-tert-butoxycarbonylaminocyclopropyl)phenylamino)-8-oxooctanoic acid (0.32 mmol, 130 mg) in dry tetrahydrofuran (5 mL), and the mixture was stirred for 10 min. The solid was filtered off, and O-(2-methoxy-2-propyl)hydroxylamine (0.96 mmol, 0.7 mL) was added to the filtrate. The solution was stirred for 15 min at 0° C., then a 6 N HC1 solution (10 mL) was added, and the stirring was continued for further 12 h. Therefore the precipitate was filtered and washed with diethyl ether (3×10 mL) to give the pure N1-(4-(2-aminocyclopropyl)phenyl)-N8-hydroxyoctanediamide hydrochloride (9).

Provenance & Evidence