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

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Reaction Steps

A mixture of 2-(2-methoxycarbonylethyl)-4-tert-butoxycarbonylaminomethylaniline (3.4 g), (S)-9-chloro-5-carboxymethyl-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione (2.80 g, 9.5 mmol), triethylamine (2.43 g, 24 mmol), and Bop-Cl (2.42 g, 9.5 mmol) in dichloromethane (40 mL) was stirred for 2 h at room temperature and diluted with ethyl acetate (800 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 recrystallized from acetone-ethyl acetate to give 3.22 g of the title compound. The mother liquid was concentrated and the residue was purified by silica gel column chromatography with ethyl acetate to 1% AcOH/ethyl acetate to give additionally 0.8 g of the title compound (72%).

Provenance & Evidence