Triethylamine → (5S)-9-Bromo-5-[p-tert-butoxycarbonylaminomethyl-o-(1-methoxycarbonyl-1acetoxymethyl) phenylcarbamoylmethyl]-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione

Participants

Reaction Steps

A mixture of 4-tert-butoxycarbonylaminomethyl-2-(1-methoxycarbonyl-1-acetoxymethyl)aniline (500 mg, 1 mmol), (S)-9-bromo-5-carboxymethyl-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione (475 mg, 1.4 mmol), triethylamine (0.55 mL), and Bop-Cl (360 mg, 1.4 mmol) in dichloromethane (15 mL) was stirred for 48 h at room temperature and diluted with ethyl acetate (200 mL). The mixture was washed with 5% potassium hydrogen sulfate, water, 1/15 phosphate buffer (pH 7.5), water, and brine, successively, dried over magnesium sulfate, and concentrated. The residue was purified by silica gel column chromatography with 0.3% acetic acid/ethyl acetate to give 340 mg of the title compound (50%).

Provenance & Evidence