Pyrrole-2-Carboxylic Acid → HCID 69818121, compound

Participants

Reaction Steps

To a stirred suspension of (2S)-3-(4-aminophenyl)-2-[N-benzyl-N-[(2S)-3-[4-(benzyloxy)phenoxy]-2-hydroxypropyl]amino]-1-propanol (51.3 mg), 1H-pyrrole-2-carboxylic acid (11.9 mg) and 1-hydroxybenzotriazole hydrate (13.5 mg) in 1,2-dichloromethane (1.0 ml) was added 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (21.5 mg) under ice-cooling and the resulting mixture was stirred at room temperature overnight. The mixture was diluted with saturated aqueous sodium hydrogencarbonate solution and extracted twice with ethyl acetate. The extracts were combined, washed twice with brine, dried over magnesium sulfate, and concentrated in vacuo. The residue was purified by preparative thin layer chromatography (eluent: toluen/ethyl acetate=5/5) to give N-[4-[(2S)-2-[N-benzyl-N-[(2S)-3-[4-(benzyloxy)phenoxy]-2-hydroxypropyl]-amino]-3-hydroxypropyl]phenyl]-1H-pyrrole-2-carboxamide (43 mg) as a gum.

Provenance & Evidence