Sodium hydride → 4-fluorobenzyl N-methyl-(2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl)carbamate

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Reaction Steps

4-Fluorobenzyl [3-(2-chloro-4-nitroimidazol-1-yl)-2-hydroxy-2-methylpropyl]-N-methylcarbamate prepared in Example 212 (1.683 g, 4.20 mmol) was dissolved in 1,4-dioxane (30 ml). To the solution, sodium hydride (0.185 g, 4.62 mmol) was added followed by stirring at room temperature for 1 hour and then stirred under reflux for 7 hours. The reaction mixture was concentrated under reduced pressure. To the residue, water was added, and the precipitates were filtered off and purified by silica gel column chromatography (n-hexane/acetone=2/1). The resulting solid was treated with a mixture of n-hexane and ethyl acetate to afford 4-fluorobenzyl N-methyl-(2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl)carbamate (0.381 g, yield 25%) as a colorless solid.

Provenance & Evidence