Sodium hydride → HCID 69635394, compound

Participants

Reaction Steps

Tert-butyl (R)-4-[3-(2-chloro-4-nitroimidazol-1-yl)-2-hydroxypropyl]piperazine-1-carboxylate prepared in Example 364 (6.43 g, 16.49 mmol) was dissolved in 1,4-dioxane (35 ml). To the solution, sodium hydride (730 mg, 18.25 mmol) was added with cooling on ice-bath, and the resulting solution was stirred at room temperature overnight and then stirred under reflux for 24 hours. The reaction mixture was allowed to return to room temperature and concentrated under reduced pressure. To the residue, water was added slowly, the mixture was extracted with methylene chloride twice, dried over sodium sulfate and then filtered. The filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate) to afford tert-butyl (R)-4-(6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl)piperazine-1-carboxylate (1.23 g, yield 21%) as a white powder.

Provenance & Evidence