Sodium hydride → HCID 23081231, compound

HRID 856280Notes

Reaction equation

HRID 856280 reaction equation
Cl[C:2]1[N:3]([CH2:10][C:11]([OH:30])([CH3:29])[CH2:12][N:13]2[CH2:18][CH2:17][N:16]([C:19]([O:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[O:20])[CH2:15][CH2:14]2)[CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=1.[H-].[Na+]>O1CCOCC1>[CH3:29][C:11]1([CH2:12][N:13]2[CH2:18][CH2:17][N:16]([C:19]([O:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[O:20])[CH2:15][CH2:14]2)[O:30][C:2]2=[N:6][C:5]([N+:7]([O-:9])=[O:8])=[CH:4][N:3]2[CH2:10]1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 23081201HCID 23081201, compound

Product 1

HCID 23081231HCID 23081231, compoundYield 52.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

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.

Workup

  1. additionwas added
  2. temperatureunder reflux for 14 hours
  3. customto return to room temperature
  4. concentrationconcentrated under reduced pressure
  5. additionTo the residue, water was added
  6. extractionthe solution was extracted with methylene chloride twice
  7. washThe organic phases were washed with a saturated saline solution
  8. dry with materialdried over magnesium 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-1c561adccb0045dabcf505bb3a398914
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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