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

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Reaction Steps

A mixture of methyl 4-tert-butoxycarbonylaminomethyl-2-methoxycarbonylmethylaniline (1.20 g, 4.27 mmol), (S)-9-chloro-5-carboxymethyl-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione (1.26 g, 4.27 mmol), triethylamine (1.49 mL, 10.7 mmol), and Bop-Cl (1.19 g, 4.69 mmol) in dichloromethane (26 mL) was stirred for 4.5 h at 0° C. to room temperature and diluted with ethyl acetate. The mixture was washed successively with 5% potassium hydrogen sulfate, water, 1/15 phosphate buffer (pH 7.5), water, and brine, dried over magnesium sulfate, and concentrated. The residual solid was washed with a 1:1 mixture of diethyl ether and dichloromethane, and dried to give 1.82 g of the title compound (74%).

Provenance & Evidence