m-Chloroperbenzoic acid → Tert-butyl-2-{2-[2-(2-methoxyethyl)-5-oxido-1h-imidazo[4,5-c]quinolin-1-yl]ethoxy}ethylcarbamate

HRID 1432298Notes

Reaction equation

HRID 1432298 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][C:5]1[N:6]([CH2:18][CH2:19][O:20][CH2:21][CH2:22][NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[C:7]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[CH:9][C:8]=2[N:17]=1.ClC1C=C(C=CC=1)C(OO)=[O:36]>C(Cl)(Cl)Cl>[CH3:1][O:2][CH2:3][CH2:4][C:5]1[N:6]([CH2:18][CH2:19][O:20][CH2:21][CH2:22][NH:23][C:24](=[O:30])[O:25][C:26]([CH3:27])([CH3:29])[CH3:28])[C:7]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N+:10]([O-:36])=[CH:9][C:8]=2[N:17]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 12106201tert-butyl 2-{2-[2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl]ethoxy}ethylcarbamate

Product 1

HCID 12106202Tert-butyl-2-{2-[2-(2-methoxyethyl)-5-oxido-1h-imidazo[4,5-c]quinolin-1-yl]ethoxy}ethylcarbamateYield 99.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of tert-butyl 2-{2-[2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl]ethoxy}ethylcarbamate (10.22 g, 24.7 mmol) in 250 mL of CHCl3 was treated with 3-chloroperoxybenzoic acid (MCPBA, 77%, 9.12 g, 40.8 mmol). After stirring 30 min, the reaction mixture was washed with 1% Na2CO3 solution (2×75 mL) and brine. The organic layer was then dried over Na2SO4 and concentrated to give 10.6 g of tert-butyl 2-{2-[2-(2-methoxyethyl)-5-oxido-1H-imidazo[4,5-c]quinolin-1-yl]ethoxy}ethylcarbamate as an orange foam that was used without further purification.

Workup

  1. washthe reaction mixture was washed with 1% Na2CO3 solution (2×75 mL) and brine
  2. dry with materialThe organic layer was then dried over Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-fddf3d0c998c42898592cf8a8736c870
Source dataset
uspto-grants-2009_11
Patent number
US07612083B2

Reaction notes

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