Sodium hydride → Tert-butyl 3-(2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-yl)propionate

HRID 856172Notes

Reaction equation

HRID 856172 reaction equation
[H-].[Na+].Cl[C:4]1[N:5]([CH2:12][C:13]([OH:24])([CH3:23])[CH2:14][CH2:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH:6]=[C:7]([N+:9]([O-:11])=[O:10])[N:8]=1>O1CCOCC1>[CH3:23][C:13]1([CH2:14][CH2:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[O:24][C:4]2=[N:8][C:7]([N+:9]([O-:11])=[O:10])=[CH:6][N:5]2[CH2:12]1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 23081446Tert-butyl 5-(2-chloro-4-nitroimidazol-1-yl)-4-hydroxy-4-methylpentanoate

Product 1

HCID 23081265Tert-butyl 3-(2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-yl)propionateYield 42.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Sodium hydride (0.12 g, 3.07 mmol) was added to a solution of tert-butyl 5-(2-chloro-4-nitroimidazol-1-yl)-4-hydroxy-4-methylpentanoate prepared in Example 43 (0.93 g, 2.79 mmol) in 1,4-dioxane (10 ml) with cooling on ice-bath followed by stirring under reflux for 7.5 hours. The reaction mixture was concentrated under reduced pressure. Water was added to the solution, and the resulting mixture was extracted with methylene chloride. The organic phase was dried over magnesium sulfate and then concentrated under reduced pressure. The residue was treated with diethyl ether to afford tert-butyl 3-(2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-yl)propionate (0.35 g, 42%) as a white solid.

Workup

  1. temperaturewith cooling on ice-bath
  2. temperatureunder reflux for 7.5 hours
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. additionWater was added to the solution
  5. extractionthe resulting mixture was extracted with methylene chloride
  6. dry with materialThe organic phase was dried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. additionThe residue was treated with diethyl ether

Sources & evidence

ORD record
ord-fe034eafcc4b4f4594d215ad053e70b4
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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