m-Chloroperbenzoic acid → HCID 67051010, compound

HRID 598377Notes

Reaction equation

HRID 598377 reaction equation
C1C=C(Cl)C=C(C(OO)=[O:9])C=1.[CH2:12]([O:19][C:20]1[CH:29]=[CH:28][C:27]2[N:26]=[CH:25][C:24]3[N:30]=[C:31]([CH2:46][O:47][CH2:48][CH3:49])[N:32]([CH2:33][C:34]([NH:37][C:38]([CH:40]4[CH2:45][CH2:44][CH2:43][CH2:42][CH2:41]4)=[O:39])([CH3:36])[CH3:35])[C:23]=3[C:22]=2[CH:21]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(Cl)(Cl)Cl>[CH2:12]([O:19][C:20]1[CH:29]=[CH:28][C:27]2[N+:26]([O-:9])=[CH:25][C:24]3[N:30]=[C:31]([CH2:46][O:47][CH2:48][CH3:49])[N:32]([CH2:33][C:34]([NH:37][C:38]([CH:40]4[CH2:41][CH2:42][CH2:43][CH2:44][CH2:45]4)=[O:39])([CH3:36])[CH3:35])[C:23]=3[C:22]=2[CH:21]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 67051137HCID 67051137, compound

Product 1

HCID 67051010HCID 67051010, compoundYield 111%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

mCPBA (60% pure, 1.34 g) was added to a solution of N-{2-[8-(benzyloxy)-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]-1,1-dimethylethyl}cyclohexanecarboxamide (2.34 g, 4.55 mmol) in chloroform (100 mL). The reaction was stirred for 2 hours and quenched by adding 50 mL of aqueous 2% sodium carbonate. The layers were separated and the aqueous fraction was extracted with two portions of chloroform. The combined organic fractions were washed with brine, dried over sodium sulfate, filtered, and concentrated to give 2.68 g of crude N-{2-[8-(benzyloxy)-2-(ethoxymethyl)-5-oxido-1H-imidazo[4,5-c]quinolin-1-yl]-1,1-dimethylethyl}cyclohexanecarboxamide as an orange foam.

Workup

  1. customquenched
  2. additionby adding 50 mL of aqueous 2% sodium carbonate
  3. customThe layers were separated
  4. extractionthe aqueous fraction was extracted with two portions of chloroform
  5. washThe combined organic fractions were washed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-fa61f7c6120d493bad51b5286ec14c1e
Source dataset
uspto-grants-2011_03
Patent number
US07897597B2

Reaction notes

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