Sodium Acetate → HCID 23081148, compound

HRID 856248Notes

Reaction equation

HRID 856248 reaction equation
Cl[C:2]1[NH:3][CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=1.[CH3:10][N:11]([CH:19]1[CH2:24][CH2:23][N:22]([CH2:25][C:26]2([CH3:29])[CH2:28][O:27]2)[CH2:21][CH2:20]1)[C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15].C([O-])(=O)C.[Na+]>C(O)CC>[CH3:10][N:11]([CH:19]1[CH2:24][CH2:23][N:22]([CH2:25][C:26]2([CH3:29])[O:27][C:2]3=[N:6][C:5]([N+:7]([O-:9])=[O:8])=[CH:4][N:3]3[CH2:28]2)[CH2:21][CH2:20]1)[C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:15])[CH3:16]

Participants

5

Reactant 3

HCID 517045Sodium AcetateHCID 86604797HCID 86604797, compoundHCID 178526855HCID 178526855, compound

Product 1

HCID 23081148HCID 23081148, compoundYield 12%

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Procedure

2-Chloro-4-nitro-1H-imidazole (1.08 g, 7.31 mmol), tert-butyl N-methyl-[1-(2-methyloxiran-2-yl-methyl)piperidin-4-yl]carbamate (2.08 g, 7.31 mmol) and sodium acetate (660 mg, 8.04 mmol) in 1-propanol (15 ml) were stirred under reflux overnight. The reaction mixture was concentrated under reduced pressure. The residue was added water, and the mixture was extracted with methylene chloride. The organic phase was dried over sodium sulfate and then filtered. The resulting filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (methylene chloride/methanol=200/1), crystallized from methylene chloride-isopropyl ether to afford tert-butyl N-methyl-[1-(2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl)piperidin-4-yl]carbamate (348 mg, yield 12%) as a white powder.

Workup

  1. temperatureunder reflux overnight
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionThe residue was added water
  4. extractionthe mixture was extracted with methylene chloride
  5. dry with materialThe organic phase was dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationThe resulting filtrate was concentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (methylene chloride/methanol=200/1)
  9. customcrystallized from methylene chloride-isopropyl ether

Sources & evidence

ORD record
ord-2d7e039357fb44d08659a7227571063d
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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