m-Chloroperbenzoic acid → tert-butyl {4-[7-benzyloxy-5-oxido-1-(2-phenoxyethyl)-1H-imidazo[4,5-c]quinolin-2-yl]butyl}carbamate

HRID 598280Notes

Reaction equation

HRID 598280 reaction equation
C1C=C(Cl)C=C(C(OO)=[O:9])C=1.[CH2:12]([O:19][C:20]1[CH:21]=[CH:22][C:23]2[C:24]3[N:32]([CH2:33][CH2:34][O:35][C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)[C:31]([CH2:42][CH2:43][CH2:44][CH2:45][NH:46][C:47](=[O:53])[O:48][C:49]([CH3:52])([CH3:51])[CH3:50])=[N:30][C:25]=3[CH:26]=[N:27][C:28]=2[CH:29]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>ClCCl>[CH2:12]([O:19][C:20]1[CH:21]=[CH:22][C:23]2[C:24]3[N:32]([CH2:33][CH2:34][O:35][C:36]4[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=4)[C:31]([CH2:42][CH2:43][CH2:44][CH2:45][NH:46][C:47](=[O:53])[O:48][C:49]([CH3:50])([CH3:52])[CH3:51])=[N:30][C:25]=3[CH:26]=[N+:27]([O-:9])[C:28]=2[CH:29]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acid2×HCID 86626156tert-butyl {4-[7-benzyloxy-1-(2-phenoxyethyl)-1H-imidazo[4,5-c]quinolin-2-yl]butyl}carbamate

Product 1

HCID 86626157tert-butyl {4-[7-benzyloxy-5-oxido-1-(2-phenoxyethyl)-1H-imidazo[4,5-c]quinolin-2-yl]butyl}carbamateYield 96.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

mCPBA (77% pure, 0.36 g, 1.6 mmol) was added to a solution of tert-butyl {4-[7-benzyloxy-1-(2-phenoxyethyl)-1H-imidazo[4,5-c]quinolin-2-yl]butyl}carbamate (0.89 g, 1.6 mmol) in dichloromethane (50 mL), and the reaction was stirred for 2.5 hours under a nitrogen atmosphere. Additional mCPBA (150 mg) was added, and the reaction was stirred over two nights. The solution was washed with water, saturated aqueous sodium bicarbonate, water, and brine, dried over sodium sulfate, and concentrated under reduced pressure to provide 0.90 g of tert-butyl {4-[7-benzyloxy-5-oxido-1-(2-phenoxyethyl)-1H-imidazo[4,5-c]quinolin-2-yl]butyl}carbamate as a tan foam.

Workup

  1. stirringthe reaction was stirred over two nights
  2. washThe solution was washed with water, saturated aqueous sodium bicarbonate, water, and brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-64d307e10b9745fea7dbbd8b7983b75f
Source dataset
uspto-grants-2011_03
Patent number
US07897597B2

Reaction notes

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