Sodium hydride → 4-fluorobenzyl N-methyl-(2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl)carbamate

HRID 856243Notes

Reaction equation

HRID 856243 reaction equation
Cl[C:2]1[N:3]([CH2:10][C:11]([OH:27])([CH3:26])[CH2:12][N:13]([CH3:25])[C:14](=[O:24])[O:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)[CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=1.[H-].[Na+]>O1CCOCC1>[CH3:25][N:13]([CH2:12][C:11]1([CH3:26])[O:27][C:2]2=[N:6][C:5]([N+:7]([O-:9])=[O:8])=[CH:4][N:3]2[CH2:10]1)[C:14](=[O:24])[O:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 866048124-fluorobenzyl [3-(2-chloro-4-nitroimidazol-1-yl)-2-hydroxy-2-methylpropyl]-N-methylcarbamate

Product 1

HCID 230814224-fluorobenzyl N-methyl-(2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl)carbamateYield 25%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

4-Fluorobenzyl [3-(2-chloro-4-nitroimidazol-1-yl)-2-hydroxy-2-methylpropyl]-N-methylcarbamate prepared in Example 212 (1.683 g, 4.20 mmol) was dissolved in 1,4-dioxane (30 ml). To the solution, sodium hydride (0.185 g, 4.62 mmol) was added followed by stirring at room temperature for 1 hour and then stirred under reflux for 7 hours. The reaction mixture was concentrated under reduced pressure. To the residue, water was added, and the precipitates were filtered off and purified by silica gel column chromatography (n-hexane/acetone=2/1). The resulting solid was treated with a mixture of n-hexane and ethyl acetate to afford 4-fluorobenzyl N-methyl-(2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl)carbamate (0.381 g, yield 25%) as a colorless solid.

Workup

  1. stirringstirred
  2. temperatureunder reflux for 7 hours
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. additionTo the residue, water was added
  5. filtrationthe precipitates were filtered off
  6. custompurified by silica gel column chromatography (n-hexane/acetone=2/1)
  7. additionThe resulting solid was treated with a mixture of n-hexane and ethyl acetate

Sources & evidence

ORD record
ord-1664f45fb23c4de89e42a6ce9b868c47
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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