[(2R)-2-methyloxiranyl]methyl 4-methylbenzene-sulfonate → (R)-2-chloro-1-[2-hydroxy-2-methyl-3-(4-methylbenzenesulfonyloxy)propyl]-4-nitroimidazole

HRID 856154Notes

Reaction equation

HRID 856154 reaction equation
[Cl:1][C:2]1[NH:3][CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=1.[CH3:10][C:11]1[CH:16]=[CH:15][C:14]([S:17]([O:20][CH2:21][C@@:22]2([CH3:25])[CH2:24][O:23]2)(=[O:19])=[O:18])=[CH:13][CH:12]=1>C(#N)C.[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1>[Cl:1][C:2]1[N:3]([CH2:25][C@:22]([OH:23])([CH3:24])[CH2:21][O:20][S:17]([C:14]2[CH:15]=[CH:16][C:11]([CH3:10])=[CH:12][CH:13]=2)(=[O:19])=[O:18])[CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=1

Participants

5

Reactant 2

HCID 10900803[(2R)-2-methyloxiranyl]methyl 4-methylbenzene-sulfonateHCID 178526855HCID 178526855, compound

Product 1

HCID 86604802(R)-2-chloro-1-[2-hydroxy-2-methyl-3-(4-methylbenzenesulfonyloxy)propyl]-4-nitroimidazoleYield 43%

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 6342AcetonitrileSolvent

Procedure

2-Chloro-4-nitro-1H-imidazole (18.4 g, 125 mmol) and (R)-2-methyloxiran-2-ylmethyl 4-methylbenzene sulfonate (36.2 g, 149 mmol) were suspended in acetonitrile (150 ml). Benzyl(triethyl)ammonium chloride (5.7 g, 25 mmol) was added to the suspension, and the resulting mixture was stirred under reflux for 8 hours. The reaction mixture was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (methylene chloride/ethyl acetate=20/1) to afford (R)-2-chloro-1-[2-hydroxy-2-methyl-3-(4-methylbenzenesulfonyloxy)propyl]-4-nitroimidazole (20.1 g, 43%) as a white amorphous form.

Workup

  1. temperatureunder reflux for 8 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (methylene chloride/ethyl acetate=20/1)

Sources & evidence

ORD record
ord-7817b2a2dad14a5a99621ce26d7745e1
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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