Sodium Acetate → HCID 23081625, compound

HRID 856367Notes

Reaction equation

HRID 856367 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([CH2:14][N:15]2[CH2:21][CH2:20][CH2:19][N:18]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:17][CH2:16]2)[CH2:13][O:12]1.C([O-])(=O)C.[Na+]>C(O)CC>[Cl:1][C:2]1[N:3]([CH2:13][C:11]([OH:12])([CH3:10])[CH2:14][N:15]2[CH2:21][CH2:20][CH2:19][N:18]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:17][CH2:16]2)[CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=1

Participants

5

Reactant 3

HCID 517045Sodium AcetateHCID 23081216HCID 23081216, compoundHCID 178526855HCID 178526855, compound

Product 1

HCID 23081625HCID 23081625, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Procedure

A mixture of 2-chloro-4-nitro-1H-imidazole (8.39 g, 56.88 mmol), tert-butyl 4-(2-methyloxiran-2-ylmethyl)homopiperazine-1-carboxylate (15.38 g, 56.88 mmol) and sodium acetate (5.13 g, 62.57 mmol) in 1-propanol (100 ml) was stirred under reflux for 10 hours. The reaction mixture was allowed to return to room temperature and then concentrated under reduced pressure. The residue was dissolved in methylene chloride. The solution was washed with water, dried over sodium sulfate and then filtered. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (methylene chloride/ethyl acetate=5/1) to afford tert-butyl 4-[3-(2-chloro-4-nitroimidazol-1-yl)-2-hydroxy-2-methylpropyl]homopiperazine-1-carboxylate (6.25 g, yield 27%) as a reddish yellow oil.

Workup

  1. temperatureunder reflux for 10 hours
  2. customto return to room temperature
  3. concentrationconcentrated under reduced pressure
  4. dissolutionThe residue was dissolved in methylene chloride
  5. washThe solution was washed with water
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated under reduced pressure
  9. customthe residue was purified by silica gel column chromatography (methylene chloride/ethyl acetate=5/1)

Sources & evidence

ORD record
ord-a3a28da47b5d45309a15f3d666e057ca
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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