p-Toluenesulfonic acid → HCID 10265074, compound

HRID 1609769Notes

Reaction equation

HRID 1609769 reaction equation
[N+:1]([C:4]1[N:5]=[CH:6][N:7]([C@H:9]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[C:10]([OH:12])=[O:11])[CH:8]=1)([O-:3])=[O:2].[CH3:19]C1C=CC(S(O)(=O)=O)=CC=1>CO.C(OCC)(=O)C>[CH3:19][O:11][C:10](=[O:12])[C@H:9]([N:7]1[CH:8]=[C:4]([N+:1]([O-:3])=[O:2])[N:5]=[CH:6]1)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

5

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 9881517(R)-alpha-hexyl-4-nitro-1H-imidazole-1-acetic acid

Product 1

HCID 10265074HCID 10265074, compoundYield 2,813.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

(R)-2-(4-Nitro-1H-imidazol-1-yl)-octanoic acid (16.0 g, 63.0 mmol) was dissolved in 1 L of anhydrous methanol. To this solution was added pTsOH (300 mg). The reaction was then heated to reflux for 16 hours. Upon cooling, the solvent was removed in vacuo, to give an oil that was dissolved in 300 mL of ethyl acetate. The solution was washed (2×250 mL) with saturated NaHCO3 solution. The organic was then dried (Na2SO4) and concentrated in vacuo to provide 13.2 g (78%) of (R)-methyl-2-(4-nitro-1H-imidazol-1-yl)-octanoate as an amber oil.

Workup

  1. temperatureThe reaction was then heated
  2. temperatureto reflux for 16 hours
  3. temperatureUpon cooling
  4. customthe solvent was removed in vacuo
  5. customto give an oil that
  6. washThe solution was washed (2×250 mL) with saturated NaHCO3 solution
  7. dry with materialThe organic was then dried (Na2SO4)
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-82af44f5c3e64693beba54ecbcb33f56
Source dataset
uspto-grants-1995_03
Patent number
US05401851

Reaction notes

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