Methyl iodide → methyl N-(tert-butoxycarbonyl)-N-(2-cyanoethyl)-2-methylalaninate

Participants

Reaction Steps

Methyl iodide (12.5 mL, 193.2 mmol) was added to a mixture of 2-[(tert-butoxycarbonyl)(2-cyanoethyl)amino]-2-methylpropanoic acid (16.5 g, 64.4 mmol) and KHCO3 (12.9 g, 193.2 mmol) in DMF (150 mL) and the reaction mixture was stirred at room temperature for 16 hours. After dilution with water, the solution was extracted with a 1/1 mixture of hexane/EA (2×). The combined organics were dried over magnesium sulfate and concentrated in vacuo to afford the title compound (16.5 g, 95%) as a yellow oil. 1H NMR (DMSO-d6) δ 3.61-3.55 (m, 5H), 2.71 (t, J=6.76 Hz, 2H), 1.42-1.36 (m, 15H).

Provenance & Evidence