Acetic Acid → tert-Butyl [3-({5-amino-2-[(tert-butoxycarbonyl)amino]phenyl}ethynyl)phenyl]carbamate

Participants

Reaction Conditions

Reaction Steps

Into the reaction flask was added tert-butyl [3-({2-[(tert-butoxycarbonyl)amino]-5-nitrophenyl}ethynyl)phenyl]carbamate (2.7 g, 6.0 mmol), methanol (70 mL), acetic acid (10 mL), and water (7 mL). Then iron powder (1.8 g, 30 mmol) was added. The reaction mixture was heated at 60° C. for 3 h. After filtration, the cake was rinsed with EtOAc. The filtrate was concentrated and the residue was diluted with NaHCO3 (aq) and EtOAc. After the layers were separated, the organic layer was dried, filtered and concentrated to give the desired product (2.3 g, 91%). LCMS for C24H30N3O4 (M+H)+: m/z=424.2.

Provenance & Evidence