Potassium Carbonate → Tert-butyl 2-(4-nitro-1H-imidazol-1-YL)ethylcarbamate

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Reaction Steps

A mixture of methanesulfonic acid 2-tert-butoxycarbonylamino-ethyl ester (compound 39.1; 2.04 g, 8.53 mmol, prepared according to the procedure of Hey, M. P. et. al J. Med. Chem 37, 1994, 381), 4-nitroimidazole (876 mg, 7.75 mmol), K2CO3 (1.18 g, 8.53 mmol), in DMF is stirred at 110° C. for 2 hours. After cooling to room temperature, the mixture is diluted with EtOAc and washed with water. The aqueous layer was extracted three times with EtOAc and the combined organic phases were dried (Na2SO4) and concentrated. The crude residue was purified by flash column chromatography (SiO2, 45 to 100% EtOAc in hexanes) to yield 634 mg (32%) of [2-(4-nitro-imidazol-1-yl)-ethyl]-carbamic acid tert-butyl ester (compound 39.2) as a solid, ES (+) MS m/e=257 (M+H+).

Provenance & Evidence