We describe the kinetic resolution of a readily available 2-pyridyl ester via an amide bond formation catalyzed by a chiral Bronsted acid. A chiral phosphoric acid bearing a 2,4,6-trimethyl-3,S-dinitrophenyl group at the 3,3'-position enabled this transformation with high selectivities. We also found that the addition of Lewis acid increased both the reactivity and selectivity in the substrate with a methoxy group.