Water → [7-benzyloxy-1-(2-hydroxy-2-methylpropyl)-5-oxido-1H-imidazo[4,5-c]quinolin-2-yl]methyl acetate

HRID 598299Notes

Reaction equation

HRID 598299 reaction equation
F.[C:2]([O:5][CH2:6][C:7]1[N:8]([CH2:28][C:29]([OH:32])([CH3:31])[CH3:30])[C:9]2[C:18]3[CH:17]=[CH:16][C:15]([O:19][CH2:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)=[CH:14][C:13]=3[N:12]=[CH:11][C:10]=2[N:27]=1)(=[O:4])[CH3:3].C1C=C(Cl)C=C(C(OO)=[O:41])C=1.O>CN(C=O)C.CO>[C:2]([O:5][CH2:6][C:7]1[N:8]([CH2:28][C:29]([OH:32])([CH3:31])[CH3:30])[C:9]2[C:18]3[CH:17]=[CH:16][C:15]([O:19][CH2:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)=[CH:14][C:13]=3[N+:12]([O-:41])=[CH:11][C:10]=2[N:27]=1)(=[O:4])[CH3:3]

Participants

7

Reactant 4

HCID 962WaterHCID 14917Hydrofluoric AcidHCID 70297m-Chloroperbenzoic acidHCID 67051092[7-benzyloxy-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinolin-2-yl]methyl acetate

Product 1

HCID 67050977[7-benzyloxy-1-(2-hydroxy-2-methylpropyl)-5-oxido-1H-imidazo[4,5-c]quinolin-2-yl]methyl acetateYield 100.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

Hydrogen fluoride (7.5 g of 48%, 0.18 mol) was added to a solution of [7-benzyloxy-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinolin-2-yl]methyl acetate (40.0 g, 0.0953 mol) in DMF (910 mL) and methanol (300 mL). mCPBA (60.6 g, 0.200 mol, 57% pure) was then added in one portion, and the reaction was stirred at ambient temperature for 5.5 hours. A mixture of ice and deionized water (4 L) was then added to the reaction mixture, and the resulting mixture was stirred vigorously for 30 minutes. The solid product was isolated by filtration, washed with deionized water, and dried under vacuum at 50° C. The solid was then triturated with diethyl ether (500 mL) for one hour, isolated by filtration, washed with diethyl ether (400 mL), and dried under vacuum at 40° C. to provide 41.7 g of [7-benzyloxy-1-(2-hydroxy-2-methylpropyl)-5-oxido-1H-imidazo[4,5-c]quinolin-2-yl]methyl acetate.

Workup

  1. additionwas then added to the reaction mixture
  2. stirringthe resulting mixture was stirred vigorously for 30 minutes
  3. customThe solid product was isolated by filtration
  4. washwashed with deionized water
  5. customdried under vacuum at 50° C
  6. customThe solid was then triturated with diethyl ether (500 mL) for one hour
  7. customisolated by filtration
  8. washwashed with diethyl ether (400 mL)
  9. customdried under vacuum at 40° C.

Sources & evidence

ORD record
ord-82d81ca942b74e6396281e19f895e74b
Source dataset
uspto-grants-2011_03
Patent number
US07897597B2

Reaction notes

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