Glycidyl tosylate, (R)- → HCID 86604800, compound

HRID 856149Notes

Reaction equation

HRID 856149 reaction equation
[Cl:1][C:2]1[NH:3][CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=1.[S:10]([C:18]1[CH:24]=[CH:23][C:21]([CH3:22])=[CH:20][CH:19]=1)([O:13][CH2:14][C@@H:15]1[O:17][CH2:16]1)(=[O:12])=[O:11].C(=O)([O-])O.[Na+]>C(#N)C>[Cl:1][C:2]1[N:3]([CH2:16][C@@H:15]([OH:17])[CH2:14][O:13][S:10]([C:18]2[CH:24]=[CH:23][C:21]([CH3:22])=[CH:20][CH:19]=2)(=[O:12])=[O:11])[CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=1

Participants

5

Reactant 3

HCID 154187Glycidyl tosylate, (R)-HCID 516892Sodium BicarbonateHCID 178526855HCID 178526855, compound

Product 1

HCID 86604800HCID 86604800, compoundYield 66.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-Chloro-4-nitro-1H-imidazole (10 g, 67.79 mmol) and (R)-(−)-glycidyl tosylate (17.02 g, 74.58 mmol) were dissolved in acetonitrile (50 ml), sodium hydrogencarbonate (6.26 g, 74.15 mmol) was added to the solution, and the resulting mixture was stirred under reflux for 3.5 hours. The reaction mixture was allowed to return to room temperature. After filtration, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/n-hexane=1/2) to afford (R)-2-chloro-1-[2-hydroxy-3-(4-methylbenzenesulfonyloxy)propyl]-4-nitroimidazole (16.9 g, yield 66%) as a light yellow oil.

Workup

  1. temperatureunder reflux for 3.5 hours
  2. customto return to room temperature
  3. filtrationAfter filtration
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate/n-hexane=1/2)

Sources & evidence

ORD record
ord-cc70c9e6cac941f8b1b53043eca39291
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

Loading…