Sodium hydride → HCID 23081231, compound

Participants

Reaction Steps

To a mixture of benzyl 4-[3-(2-chloro-4-nitroimidazol-1-yl)-2-hydroxy-2-methylpropyl]-piperazine-1-carboxylate prepared in Example 315 (55.22 g, 126.11 mmol) and 1,4-dioxane (550 ml), sodium hydride (6.05 g, 151.25 mmol) was added followed by stirring under reflux for 14 hours. The reaction mixture was allowed to return to room temperature and concentrated under reduced pressure. To the residue, water was added, and the solution was extracted with methylene chloride twice. The organic phases were washed with a saturated saline solution, dried over magnesium sulfate and then filtered. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate) to afford benzyl 4-(2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl)piperazine-1-carboxylate (26.54 g, yield 52%) as a white powder.

Provenance & Evidence