Lithium hydroxide, monohydrate → 2-Carbamoyl-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-4-carboxylic acid

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Reaction Steps

Methyl 2-cyano-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-4-carboxylate (3 g, 10.7 mmol) was dissolved in THF (30 ml) and H2O (8 ml). LiOH.H2O (1.1 g, 16.1 mmol) was added to the solution and the mixture was stirred at RT overnight. The reaction mixture was concentrated and acidified to pH 2 using 1 N HCl. The mixture was extracted with EtOAc and the organic layer was concentrated. Yield 2.2 g. 1H-NMR (400 MHz; DMSO-d6): δ −0.06 (s, 9H), 0.85 (t, 2H), 2.57 (s, 3H), 3.52 (t, 2H), 5.79 (s, 2H), 7.66 (s, 1H), 7.96 (s, 1H), 8.09 (s, 1H), 12.68 (s, 1H).

Provenance & Evidence