4'-(Aminomethyl)-biphenyl-2-carboxylic acid 1,1-dimethylethyl ester → 4'-[3-(t-Butoxycarbonylaminomethyl)-5-propyl-[1,2,4]-triazol-4-ylmethyl]biphenyl-2-carboxylic acid t-butyl ester

Participants

Reaction Conditions

Reaction Steps

4′-Aminomethylbiphenyl-2-carboxylic acid t-butyl ester (1.5 g, 5.2 mmol) and [1-ethoxy-but-(E)-ylidene-hydrazinocarbonylmethyl] carbamic acid t-butyl ester (1.0 g, 3.5 mmol) were combined and dissolved in ethanol (50 mL). The mixture was heated at 50° C. for 2 hours and then 70° C. overnight. The mixture was then cooled and concentrated. The product was purified by silica gel chromatography (0-20% MeOH:DCM) to obtain intermediate (23a) (400 g). MS m/z: [M+H+] calcd for C29H38N4O4, 507.6; found 507.3.

Provenance & Evidence