Iodoethane → 2-Benzyloxycarbonylamino-4-carbamoyl-butyric acid ethyl ester

Participants

Reaction Steps

A mixture of acid (1) (64 g, 0.228 mol), dimeththylformamide (210 ml) and sodium bicarbonate (111 g, 1.32 mol, 5.8 equiv.) was stirred at room temperature for 30 min. Ethyl iodide (34 ml, 66.3 g, 0.425 mol, 1.86 equiv.) was added and stirring was continued overnight under nitrogen. The reaction mixture was slowly diluted with water to 1 L and stirred for 40 min. The solid was collected by filtration, washed well with water and partitioned between ethyl acetate (8 L) and water (3 L). Phases were separated and the aqueous phase was extracted with ethyl acetate (2.5 L). The combined organic extracts were washed with water (1 L), dried over sodium sulfate, stripped and dried in a vacuum oven (50° C.) to produce (2) (47 g, 66.7%).

Provenance & Evidence