Methyl 3-({3-[(tert-butoxycarbonyl)amino]phenyl}ethynyl)-5-nitrobenzoate → Methyl 3-amino-5-(2-{3-[(tert-butoxycarbonyl)amino]phenyl}ethyl)benzoate

Participants

Reaction Steps

To a solution of methyl 3-({3-[(tert-butoxycarbonyl)amino]phenyl}ethynyl)-5-nitrobenzoate (1.85 g, 4.67 mmol) in methanol (50 mL) was added 10% palladium on carbon (1.85 g, 1.58 mmol), and the mixture was hydrogenated under 55 psi of H2 for 72 hours with shaking. The solution was filtered through a pad of celite, and filtrate was concentrated. The residue was purified by flash column chromatography to give the desired product as a yellow oil (1.70 g, 98%). LCMS for C21H27N2O4 (M+H)+: m/z=371.1.

Provenance & Evidence