Sodium hydride → HCID 69481875, compound

Participants

Reaction Steps

To the solution of (R)-3-(2-chloro-4-nitroimidazol-1-yl)-2-hydroxy-2-methylpropyl 6-chloro-3,4-dihydro-2H-quinoline-1-carboxylate prepared in Example 116 (1.84 g, 4.29 mmol) in DMF (10 ml), sodium hydride (0.21 g, 5.15 mmol) was added followed by stirring for 1 hour with cooling on ice-bath. To the reaction mixture, ice-water was added, the solution was extracted with ethyl acetate. The organic phase was washed with water, dried over magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (methylene chloride/ethyl acetate=9/1) and recrystallized from acetonitrile-isopropanol to afford (R)-2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl 6-chloro-3,4-dihydro-2H-quinoline-1-carboxylate (0.68 g, yield 40%) as a white solid.

Provenance & Evidence