Sodium hydride → HCID 69635394, compound

HRID 856303Notes

Reaction equation

HRID 856303 reaction equation
Cl[C:2]1[N:3]([CH2:10][C@H:11]([OH:26])[CH2:12][N:13]2[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]2)[CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=1.[H-].[Na+]>O1CCOCC1>[N+:7]([C:5]1[N:6]=[C:2]2[N:3]([CH:4]=1)[CH2:10][C@@H:11]([CH2:12][N:13]1[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]1)[O:26]2)([O-:9])=[O:8]

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 69635205HCID 69635205, compound

Product 1

HCID 69635394HCID 69635394, compoundYield 21.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

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.

Workup

  1. temperaturewith cooling on ice-bath
  2. stirringstirred
  3. temperatureunder reflux for 24 hours
  4. customto return to room temperature
  5. concentrationconcentrated under reduced pressure
  6. additionTo the residue, water was added slowly
  7. extractionthe mixture was extracted with methylene chloride twice
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. concentrationThe filtrate was concentrated under reduced pressure
  11. customThe residue was purified by silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-dff6fb72d8224091829958362121669f
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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