Aminoacetaldehyde dimethyl acetal → N-(Ethyl carboxymethyl)-N'-(2,2-dimethoxyethyl)oxamide

Participants

Reaction Steps

To a solution of the oxamate 9-1 (84.0 g, 414 mmol) in 2-propanol (500 ml) was added aminoacetaldehyde dimethyl acetal (45.7 g, 435 mmol) in one portion. After stirring overnight at room temperature, the reaction mixture was concentrated to a thick orange oil. This thick slurry was diluted with 2-propanol (300 ml) and the solid was broken up with a spatula. Filtration afforded a solid which was further rinsed with an additional portion of 2-propanol. Removal of residual 2-propanol was accomplished via high vacuum to afford a light orange solid 9-2: 1H NMR (CDCl3) δ7.82 (br s, 1H), 7.50 (br s, 1H), 4.41 (t, 1H, 5.3 Hz), 4.24 (q, 2H, 7.1 Hz), 4.09 (d, 2H, 5.9 Hz), 3.47 (dd, 2H, 5.3, 6.2 Hz), 3.40 (s, 6H), 1.30 (t, 3 H, 7.1 Hz).

Provenance & Evidence