Triethylamine → HCID 70236198, compound

Participants

Reaction Steps

To a solution of L-aspartic acid dimethyl ester hydrochloride (2.0 g, 10 mmol) in chloroform (100 mL) was added isonicotinoyl chloride hydrochloride (1.8 g, 10 mmol) and triethylamine (3.0 mL, 21.5 mmol). The reaction mixture was refluxed for 2 h, and then stirred at room temperature for 24 h. The solution was filtered and the filtrate was evaporated to give a whitish oil. This residue was dissolved in 20 mL H2O, and was then extracted with ethyl acetate (2×100 mL). The organic phases were combined, washed with H2O (50 mL), and dried over Na2SO4. Removal of ethyl acetate gave a whitish oil, isonicotinoyl aspartic acid dimethyl ester. Electrospray MS: m/z=267 (M+1, [C12H14N2O5]+) 1H NMR (CDCl3): 2.91-3.17 (m, 2H, CH2), 3.69 (s, 3H, COOCH3), 3.78 (s, 3H, COOCH3), 4.99-5.05 (m, 1H, CH), 7.38-7.41 (d, 1H, NH), 7.62-7.65 (m, 2H, py), 7.82-7.84 (m, 2H, py).

Provenance & Evidence