Ethyl bromoacetate → Ethyl N-(2-((tert-butoxycarbonyl)amino)ethyl)-N-methylglycinate

Participants

Reaction Steps

Ethyl bromoacetate (1.27 ml, 11.48 mmol) was added to a mixture of tert-butyl(2-(methylamino)ethyl)carbamate (2.0 g, 11.48 mmol), triethylamine (4.81 ml) and THF (24 ml) at 0° C. After stirring 24 h at room temperature the reaction mixture was partitioned between saturated aqueous NaHCO3 and DCM, extracted 2× with DCM, the organic layers dried over Na2SO4 and evaporated to give the title compound as a clear pale-yellow oil. 1H NMR (400 MHz, CDCl3) δ 5.20 (s, br, 1H), 4.18 (q, 2H), 3.24 (s, 2H), 3.22-3.16 (m, 2H), 2.65-2.61 (m, 2H), 2.38 (s, 3H), 1.42 (s, 9H), 1.24 (t, 3H).

Provenance & Evidence