Peracetic Acid → HCID 67051109, compound

HRID 2383153Notes

Reaction equation

HRID 2383153 reaction equation
C(OO)(=[O:3])C.[CH2:6]([O:13][C:14]1[CH:23]=[CH:22][C:21]2[N:20]=[CH:19][C:18]3[N:24]=[C:25]([CH2:32][O:33][CH2:34][CH3:35])[N:26]([CH2:27][C:28]([CH3:31])([OH:30])[CH3:29])[C:17]=3[C:16]=2[CH:15]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>C(OCC)(=O)C>[CH2:6]([O:13][C:14]1[CH:23]=[CH:22][C:21]2[N+:20]([O-:3])=[CH:19][C:18]3[N:24]=[C:25]([CH2:32][O:33][CH2:34][CH3:35])[N:26]([CH2:27][C:28]([CH3:29])([OH:30])[CH3:31])[C:17]=3[C:16]=2[CH:15]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 6585Peracetic AcidHCID 67051044HCID 67051044, compound

Product 1

HCID 67051109HCID 67051109, compoundYield 72.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Peracetic acid (2.0 mL of 32% by weight in dilute acetic acid, 9.5 mmol) was added to a solution of (8-benzyloxy-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-ol (2.5 g, 6.2 mmol) in ethyl acetate (400 mL), and the reaction was stirred for two days at ambient temperature. The volatiles were removed under reduced pressure, and the residue was dissolved in dichloromethane. The resulting solution was washed with aqueous sodium bicarbonate and water, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The crude product was recrystallized from a mixture of ethyl acetate, hexanes, and 2-propanol and then purified by column chromatography on a HORIZON HPFC system (silica gel cartridge, eluting with dichloromethane:methanol ranging in ratios from 98:2 to 90:10) to provide 1.9 g of (8-benzyloxy-2-ethoxymethyl-5-oxido-1H-imidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-ol as a solid, mp 228-230° C.

Workup

  1. customThe volatiles were removed under reduced pressure
  2. dissolutionthe residue was dissolved in dichloromethane
  3. washThe resulting solution was washed with aqueous sodium bicarbonate and water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was recrystallized from a mixture of ethyl acetate, hexanes, and 2-propanol
  8. custompurified by column chromatography on a HORIZON HPFC system (silica gel cartridge, eluting with dichloromethane:methanol ranging in ratios from 98:2 to 90:10)

Sources & evidence

ORD record
ord-7ab30b0e0aea4e46bb82464ca5f37d85
Source dataset
uspto-grants-2012_09
Patent number
US08263594B2

Reaction notes

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