Water → Benzyl{4-[({3-[(tert-butoxycarbonyl)amino]-6-phenylpyridin-2-yl}amino)carbonyl]benzyl}carbamate

Participants

Reaction Conditions

Reaction Steps

Benzyl chloroformate (0.06 ml, 0.420 mmol) was added to a flask containing tert-butyl(2-{[4-(aminomethyl)benzoyl]amino}-6-phenylpyridin-3-yl)carbamate (158 mg, 0.378 mmol) and DIPEA (0.15 ml, 0.859 mmol) in THF (5 mL) at 0° C. The mixture was stirred at 0° C. for 1 hour. Water was added and the products were extracted into EtOAc (2×). The combined organic extracts were washed with brine, dried over sodium sulfate and concentrated. The organic product was purified by column chromatography on silica gel Biotage 25S, eluting with EtOAc/hexanes (0%-100%) to give a pale slightly yellow transparent gel. MS: cal'd 553 (MH+), exp 553 (MH+).

Provenance & Evidence