m-Chloroperbenzoic acid → tert-butyl [4-(2-ethyl-5-oxido-1H-imidazo[4,5-c]quinolin-1-yl)butyl]tetrahydro-2H-pyran-4-ylcarbamate

HRID 62030Notes

Reaction equation

HRID 62030 reaction equation
[C:1]([O:5][C:6](=[O:33])[N:7]([CH2:14][CH2:15][CH2:16][CH2:17][N:18]1[C:30]2[C:29]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[N:23]=[CH:22][C:21]=2[N:20]=[C:19]1[CH2:31][CH3:32])[CH:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].ClC1C=CC=C(C(OO)=[O:42])C=1>C(Cl)(Cl)Cl>[C:1]([O:5][C:6](=[O:33])[N:7]([CH2:14][CH2:15][CH2:16][CH2:17][N:18]1[C:30]2[C:29]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[N+:23]([O-:42])=[CH:22][C:21]=2[N:20]=[C:19]1[CH2:31][CH3:32])[CH:8]1[CH2:9][CH2:10][O:11][CH2:12][CH2:13]1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 67431108tert-butyl [4-(2-ethyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]tetrahydro-2H-pyran-4-ylcarbamate

Product 1

HCID 67431480tert-butyl [4-(2-ethyl-5-oxido-1H-imidazo[4,5-c]quinolin-1-yl)butyl]tetrahydro-2H-pyran-4-ylcarbamate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a solution of tert-butyl[4-(2-ethyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]tetrahydro-2H-pyran-4-ylcarbamate in chloroform was added m-chloroperbenzoic acid (4 eq.) and stirred at ambient temperature for 2 hrs. Reaction mixture was then diluted with chloroform and washed with saturated sodium bicarbonate solution. Organic layer was dried over sodium sulphate and concentrated under reduced pressure to yield sticky mass. Product was then purified using silica gel column chromatography to afford tert-butyl[4-(2-ethyl-5-oxido-1H-imidazo[4,5-c]quinolin-1-yl)butyl]tetrahydro-2H-pyran-4-ylcarbamate.

Workup

  1. customReaction mixture
  2. washwashed with saturated sodium bicarbonate solution
  3. dry with materialOrganic layer was dried over sodium sulphate
  4. concentrationconcentrated under reduced pressure
  5. customto yield sticky mass
  6. customProduct was then purified

Sources & evidence

ORD record
ord-980d1dde98934d5ba9205d429b9d045f
Source dataset
uspto-grants-2016_09
Patent number
US09446040B2

Reaction notes

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