Triethylamine → HCID 86755347, compound

Participants

Reaction Steps

To a stirred solution of 2-(R,S)-(2-naphthylacetyl)amino-3-[4'-(1"-t butoxycarbonyl-1"-methyl)ethyl]benzenepropanoic acid (0.31 g, 0.66 mmol) in methylene chloride (5 mL) at rt was added dimethylformamide (3drops) followed by oxalyl chloride (2 M in methylene chloride, 0.30 mL, 0.66 mmol). The mixture was stirred at rt for 1 hour. Triethylamine (0. 13 mL), 4-amino-2-(4-methoxybenzyl)-5-methyl-3-pyridazinone (0.12 g, 0.47 mmol) and DMAP (0.005 g)were added. The mixture was stirred overnight at rt, and heated at reflux for 6 hours. The solvents were evaporated, and the residue was fractionated over silica gel (ethyl acetate/hexane 1/1) to give 4-[2'-(R,S)-2""-naphthylacetyl)amino-3'-[4"-(1'"-t butoxycarbonyl-1'"-methyl)ethyl]benzene]propanoylamino-2-(4-methoxybenzyl)-5-methyl-3-pyridazinone (0.08 g, 0.11 mmol, 17%).

Provenance & Evidence