Sodium Acetate → 4-fluorobenzyl [3-(2-chloro-4-nitroimidazol-1-yl)-2-hydroxy-2-methylpropyl]-N-methylcarbamate

HRID 856242Notes

Reaction equation

HRID 856242 reaction equation
[Cl:1][C:2]1[NH:3][CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=1.[CH3:10][N:11]([CH2:23][C:24]1([CH3:27])[CH2:26][O:25]1)[C:12](=[O:22])[O:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=1.C([O-])(=O)C.[Na+]>C(O)C>[Cl:1][C:2]1[N:3]([CH2:27][C:24]([OH:25])([CH3:26])[CH2:23][N:11]([CH3:10])[C:12](=[O:22])[O:13][CH2:14][C:15]2[CH:16]=[CH:17][C:18]([F:21])=[CH:19][CH:20]=2)[CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=1

Participants

5

Reactant 3

HCID 517045Sodium AcetateHCID 23081487HCID 23081487, compoundHCID 178526855HCID 178526855, compound

Product 1

HCID 866048124-fluorobenzyl [3-(2-chloro-4-nitroimidazol-1-yl)-2-hydroxy-2-methylpropyl]-N-methylcarbamateYield 65%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Chloro-4-nitro-1H-imidazole (0.953 g, 6.46 mmol) and 4-fluorobenzyl N-methyl-(2-methyloxiran-2-ylmethyl)carbamate (1.964 g, 7.75 mmol) were dissolved in ethanol (20 ml). To the solution, sodium acetate (0.583 g, 7.11 mmol) was added followed by stirring under reflux overnight. The reaction mixture was concentrated under reduced pressure. To the residue, ethyl acetate and water were added, and the solution was extracted with ethyl acetate. The organic phase was dried over sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=1/1) to afford 4-fluorobenzyl [3-(2-chloro-4-nitroimidazol-1-yl)-2-hydroxy-2-methylpropyl]-N-methylcarbamate (1.683 g, yield 65%) as a colorless oil.

Workup

  1. temperatureunder reflux overnight
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionTo the residue, ethyl acetate and water were added
  4. extractionthe solution was extracted with ethyl acetate
  5. dry with materialThe organic phase was dried over sodium sulfate
  6. filtrationAfter filtration
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe resulting residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-5bc3f23d1748484bb6523c4afd60973a
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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