Ethyl Acetate → (R)-2-chloro-1-(2-methyloxiran-2-ylmethyl)-4-nitroimidazole

HRID 856155Notes

Reaction equation

HRID 856155 reaction equation
[Cl:1][C:2]1[NH:3][CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=1.CC1C=CC(S(O[CH2:21][C@@:22]2([CH3:25])[CH2:24][O:23]2)(=O)=O)=CC=1.C(OCC)(=O)C.C1CCN2C(=NCCC2)CC1>C(#N)C.[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1>[Cl:1][C:2]1[N:3]([CH2:21][C@:22]2([CH3:25])[CH2:24][O:23]2)[CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 10900803[(2R)-2-methyloxiranyl]methyl 4-methylbenzene-sulfonateHCID 178526855HCID 178526855, compound

Product 1

HCID 10443353(R)-2-chloro-1-(2-methyloxiran-2-ylmethyl)-4-nitroimidazoleYield 68%

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 6342AcetonitrileSolvent

Procedure

2-Chloro-4-nitro-1H-imidazole (1.51 g, 10.17 mmol) and (R)-2-methyloxiran-2-ylmethyl 4-methylbenzene sulfonate (3.70 g, 15.25 mmol) were suspended in acetonitrile (150 ml). Benzyl(triethyl)ammonium chloride (0.23, 1.02 mmol) was added to this suspension, and the resulting mixture was stirred under reflux for 10 hours. After the reaction mixture was allowed to return to room temperature, ethyl acetate was added to the solution. The resulting mixture was washed with an aqueous sodium hydrogencarbonate, dried over magnesium sulfate and then filtered. The filtrate was concentrated under reduced pressure and dissolved in ethyl acetate (40 ml). DBU (1.57 ml, 10.17 mmol) was added to the solution with cooling on ice-bath, and the resulting mixture was stirred at room temperature for 1.5 hours. The reaction mixture was washed with water, dried over magnesium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=7/3) to afford (R)-2-chloro-1-(2-methyloxiran-2-ylmethyl)-4-nitroimidazole (1.50 g, yield 68%) as a light yellow oil.

Workup

  1. temperatureunder reflux for 10 hours
  2. customto return to room temperature
  3. washThe resulting mixture was washed with an aqueous sodium hydrogencarbonate
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. dissolutiondissolved in ethyl acetate (40 ml)
  8. temperaturewith cooling on ice-bath
  9. stirringthe resulting mixture was stirred at room temperature for 1.5 hours
  10. washThe reaction mixture was washed with water
  11. dry with materialdried over magnesium sulfate
  12. concentrationconcentrated under reduced pressure
  13. customThe residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=7/3)

Sources & evidence

ORD record
ord-d0410ab1ed6548b39b37048f2a3d303f
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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