Water → HCID 21936601, compound

HRID 432746Notes

Reaction equation

HRID 432746 reaction equation
[CH2:1]([C:3]1[N:4]([CH2:16][CH2:17][O:18][CH2:19][CH2:20][NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[C:5]2[C:14]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[N:8]=[CH:7][C:6]=2[N:15]=1)[CH3:2].ClC1C=C(C=CC=1)C(OO)=[O:34].O>C(Cl)(Cl)Cl>[CH2:1]([C:3]1[N:4]([CH2:16][CH2:17][O:18][CH2:19][CH2:20][NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[C:5]2[C:14]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[N+:8]([O-:34])=[CH:7][C:6]=2[N:15]=1)[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 70297m-Chloroperbenzoic acidHCID 21936589HCID 21936589, compound

Product 1

HCID 21936601HCID 21936601, compoundYield 100.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of tert-butyl 2-[2-(2-ethyl-1H-imidazo[4,5-c]quinolin-1-yl)ethoxy]ethylcarbamate (13.78 g 35.8 mmol) in 175 mL of CHCl3 was treated with 3-chloroperoxybenzoic acid (MCPBA, 70%, 10.28 g, 41.7 mmol). After stirring for 3 h, the reaction mixture was treated with water (100 mL) and CHCl3 (50 mL) and the layers were separated. The organic portion was washed with 1% Na2CO3 solution (2×), water and brine then dried over Na2SO4 and concentrated to give 14.35 g tert-butyl 2-[2-(2-ethyl-5-oxido-1H-imidazo[4,5-c]quinolin-1-yl)ethoxy]ethylcarbamate as a sticky tan solid.

Workup

  1. customthe layers were separated
  2. washThe organic portion was washed with 1% Na2CO3 solution (2×), water and brine
  3. dry with materialthen dried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c2db37b79e85416d89616a4f599d9472
Source dataset
uspto-grants-2003_12
Patent number
US06664265B2

Reaction notes

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