tert-Butyl [3-({2-[(tert-butoxycarbonyl)amino]-5-nitrophenyl}ethynyl)phenyl]carbamate → Carbamic acid,n-[3-[2-[5-amino-2-[[(1,1-dimethylethoxy)carbonyl]amino]phenyl]ethyl]phenyl]-,1,1-dimethylethyl ester

Participants

Reaction Steps

To a solution of tert-butyl [3-({2-[(tert-butoxycarbonyl)amino]-5-nitrophenyl}ethynyl)phenyl]carbamate (15.0 g, 33.1 mmol) in DMF (234 mL) was added 10% Palladium on carbon (13.1 g, 11.2 mmol). The solution was shaked under 55 psi H2 atmosphere for 72 h. The solution was filtered through a pad of celite. The filtrate was concentrated and purified with silica gel chromatography (45% ethyl acetate/hexanes) to give an intermediate as yellow oil. To a solution of the intermediate in methanol (200 mL) was added 10% Palladium on carbon (12 g). The resulting solution was shaked under 55 psi H2 atmosphere overnight. The reaction mixture was filtered through a pad of celite and the filtrate was concentrated. The crude product was purified with a short pad of silica gel to give the desire product (11.5 g, 81%). LCMS calculated for C24H33N3O4Na (M+Na)+: m/z=450.2.

Provenance & Evidence