Tert-butyl-(2-nitro-imidazol-1-yl)acetate → 2-(2-Nitroimidazol-1-yl)acetic acid

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Reaction Steps

Compound 2 (2.5 g) is dissolved in 20 mL of a cocktail of TFA, water, thioanisole 95-2.5-2.5 and stirred at room temperature for one night. The mixture is then concentrated under vacuum and co-evaporated several times with diethyl ether until formation of a powder. After filtration, the precipitate is washed with dichloromethane and acetonitrile to give quantitatively the expected product. Mp 143° C. (decomposition); 1H NMR (DMSO-d6, 400 MHz) δ 5.21 (s, 2H), 7.21 (d, 1H, J=1.01 Hz), 7.64 (d, 1H, J=1.01 Hz). 13C (DMSO-d6, 101 MHz) δ 50.65, 127.69, 128.44, 168.56, 168.57; MS (ESI+/ESI−) m/z 170.12 [M−H]−, 341.05 [2M−H]−, 194.14 [M+Na]+.

Provenance & Evidence