Sodium Iodide → N-2-Propen-1-ylglycine ethyl ester

Participants

Reaction Steps

To an ice cold solution of K2CO3 (331.7 g, 2.4 mol), NaI (360 g, 2.4 mol), DMF (1 L), triethylamine (484.8 g, 4.8 mol) and prop-2-en-1-amine (82 g, 1.44 mol) was slowly added a solution of ethyl bromoacetate (200 g, 1.2 mol) in DMF (100 mL) via addition funnel over 0.5 hr. The ice bath was removed upon completion of addition, and the mixture was stirred at room temperature overnight. The mixture was filtered and rinsed with Et2O. Cold saturated NaCl aq. (2 L) was added to filtrate and the mixture was extracted with Et2O (1 L*3). The combined organic extracts were dried over Na2SO4, filtered and concentrated which gave the title compound XId (150 g, 87.3%) as a yellow oil, which was directly utilized for next reaction without further purification.

Provenance & Evidence