Acetic Acid → HCID 68975745, compound

HRID 540941Notes

Reaction equation

HRID 540941 reaction equation
[CH2:1]([O:3][CH2:4][C:5]1[N:6]([CH2:29][C:30]([OH:33])([CH3:32])[CH3:31])[C:7]2[C:16]3[CH:15]=[CH:14][C:13]([O:17][CH2:18][CH2:19][NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[CH:12][C:11]=3[N:10]=[CH:9][C:8]=2[N:28]=1)[CH3:2].C(OO)(=[O:36])C.C(O)(=O)C.S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+]>C(OCC)(=O)C.O>[CH2:1]([O:3][CH2:4][C:5]1[N:6]([CH2:29][C:30]([OH:33])([CH3:32])[CH3:31])[C:7]2[C:16]3[CH:15]=[CH:14][C:13]([O:17][CH2:18][CH2:19][NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:24])[CH3:25])=[CH:12][C:11]=3[N+:10]([O-:36])=[CH:9][C:8]=2[N:28]=1)[CH3:2]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 6585Peracetic Acid2×HCID 656671Sodium PyrosulfiteHCID 68970399HCID 68970399, compound

Product 1

HCID 68975745HCID 68975745, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

tert-Butyl 2-{[2-(ethoxymethyl)-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinolin-7-yl]oxy}ethylcarbamate (2.9 g, 6.32 mmol) was dissolved in ethyl acetate (25 mL). 32% Peracetic acid in acetic acid (1.99 mL, 9.48 mmol) was added to the solution and the mixture was heated to 50° C. for 2 hours. Another 0.5 mL of the peracetic acid solution (2.37 mmol) was added and the reaction was stirred for 1 hour. A solution of sodium metabisulfite in water (1.5 g in 3.0 mL) was added in two portions and the reaction mixture was stirred for 10 minutes. The heat was then removed and the solution was brought to pH≈10 with saturated aqueous sodium carbonate (˜15 mL). The resulting precipitate was filtered, washed with ethyl acetate (10 mL) and water (10 mL), and dried under vacuum to afford 2.8 g of tert-butyl 2-{[2-(ethoxymethyl)-1-(2-hydroxy-2-methylpropyl)-5-oxido-1H-imidazo[4,5-c]quinolin-7-yl]oxy}ethylcarbamate as a white paper-like solid with some water remaining.

Workup

  1. stirringthe reaction mixture was stirred for 10 minutes
  2. customThe heat was then removed
  3. filtrationThe resulting precipitate was filtered
  4. washwashed with ethyl acetate (10 mL) and water (10 mL)
  5. customdried under vacuum

Sources & evidence

ORD record
ord-a4cc65e1c8404c80b95b90907279e9c6
Source dataset
uspto-grants-2014_10
Patent number
US08871782B2

Reaction notes

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