Sodium Iodide → HCID 69635205, compound

HRID 856294Notes

Reaction equation

HRID 856294 reaction equation
[Cl:1][C:2]1[NH:3][CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=1.S(C1C=CC(C)=CC=1)(O[CH2:14][C@H:15]1[O:17][CH2:16]1)(=O)=O.C(=O)([O-])O.[Na+].[N:30]1([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1.C(N(CC)CC)C.[I-].[Na+]>C(O)C.O.CN(C=O)C>[Cl:1][C:2]1[N:3]([CH2:14][C@H:15]([OH:17])[CH2:16][N:33]2[CH2:34][CH2:35][N:30]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[CH2:31][CH2:32]2)[CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=1

Participants

10

Reactant 6

HCID 5238Sodium IodideHCID 8471TriethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 153296Oxiranemethanol, 4-methylbenzenesulfonate, (S)-HCID 516892Sodium BicarbonateHCID 178526855HCID 178526855, compound

Product 1

HCID 69635205HCID 69635205, compoundYield 40%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-chloro-4-nitro-1H-imidazole (6.1 g, 41.35 mmol), (S)-(+)-glycidyl tosylate (12.27 g, 53.75 mmol) and sodium hydrogencarbonate (7.3 g, 86.89 mmol) in ethanol (30 ml) was stirred under reflux for 9 hours. The reaction mixture was allowed to return to room temperature, then diluted with water, and the solution was extracted with methylene chloride twice. The extract was washed with a saturated saline solution, dried over magnesium sulfate and then filtered. The filtrate was concentrated to afford a foam. The resulting foam was dissolved in DMF (60 ml). To the solution, tert-butyl piperazine-1-carboxylate (8.47 g, 45.48 mmol), triethylamine (6.92 ml, 49.64 mmol) and sodium iodide (6.82 g, 45.5 mmol) were added followed by stirring at room temperature for 24 hours. The reaction mixture was poured into water, and extracted with ethyl acetate twice. The organic phases were combined, washed with water three times, dried over magnesium sulfate and then filtered. The filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate) to afford tert-butyl (R)-4-[3-(2-chloro-4-nitroimidazol-1-yl)-2-hydroxypropyl]piperazin-1-carboxylate (6.43 g, yield 40%) as a light yellow oil.

Workup

  1. temperatureunder reflux for 9 hours
  2. customto return to room temperature
  3. extractionthe solution was extracted with methylene chloride twice
  4. washThe extract was washed with a saturated saline solution
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated
  8. customto afford a foam
  9. stirringby stirring at room temperature for 24 hours
  10. extractionextracted with ethyl acetate twice
  11. washwashed with water three times
  12. dry with materialdried over magnesium sulfate
  13. filtrationfiltered
  14. concentrationThe filtrate was concentrated under reduced pressure
  15. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-dd53aa2e85e64506bf74fad1255bf6fc
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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