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

HRID 2383107Notes

Reaction equation

HRID 2383107 reaction equation
C1C=C(Cl)C=C(C(OO)=[O:9])C=1.[C:12]([O:16][C:17](=[O:53])[NH:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]1[N:24]([CH2:44][CH2:45][O:46][C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[C:25]2[C:34]3[CH:33]=[CH:32][C:31]([O:35][CH2:36][C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)=[CH:30][C:29]=3[N:28]=[CH:27][C:26]=2[N:43]=1)([CH3:15])([CH3:14])[CH3:13]>ClCCl>[C:12]([O:16][C:17](=[O:53])[NH:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]1[N:24]([CH2:44][CH2:45][O:46][C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[C:25]2[C:34]3[CH:33]=[CH:32][C:31]([O:35][CH2:36][C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)=[CH:30][C:29]=3[N+:28]([O-:9])=[CH:27][C:26]=2[N:43]=1)([CH3:15])([CH3:13])[CH3:14]

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-d136e27bd285486aa57135c5d754be7f
Source dataset
uspto-grants-2012_09
Patent number
US08263594B2

Reaction notes

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