Application
2-(BOC-amino)isonicotinic acid methyl ester, also known as Boc-isonicotinic acid methyl ester, is an organic compound widely used in the synthesis of various compounds. It is an important intermediate in the synthesis of pharmaceuticals, agrochemicals, and other chemicals. Furthermore, 2-(BOC-amino)isonicotinic acid methyl ester is used in the synthesis of many other compounds, including amides, nitriles, and amines. It is also used in the synthesis of peptides, peptide analogs, and other peptide mimics.
Synthesis
A 500 mL round bottomed flask was charged with methyl 2-aminoisonicotinate (5.0 g, 32.9 mmol) and suspended in t-BuOH (200 mL). To this stirring solution was added di-tert-butyl dicarbonate (7.53 g, 34.5 mmol). The flask was vented and placed in an oil bath preheated to 50°C. The reaction mixture was let stir overnight. After 22 hours LCMS showed near complete conversion of starting material. The mixture was cooled to room temperature and filtered. The material was taken on without any further purification. Yield 5.93 g of white solid, Methyl 2-(Boc-amino)isonicotinate. 1H NMR (400 MHz, DMSO-d6) δ ppm 10.14 (1H, s), 8.43 (1H, dd, J=5.02, 0.75 Hz), 8.33 (1H, s), 7.45 (1H, dd, J=5.02, 1.51 Hz), 3.89 (3H, s), 1.48 (9H, s).
