Sodium Carbonate → HCID 68973272, compound

HRID 540908Notes

Reaction equation

HRID 540908 reaction equation
ClC1C=C(C=CC=1)C(OO)=[O:6].[CH2:12]([O:14][CH2:15][C:16]1[N:17]([CH2:39][CH2:40][CH3:41])[C:18]2[C:27]3[CH:26]=[C:25]([O:28][CH2:29][CH2:30][CH2:31][N:32]4[CH2:36][CH2:35][CH2:34][C:33]4=[O:37])[CH:24]=[CH:23][C:22]=3[N:21]=[CH:20][C:19]=2[N:38]=1)[CH3:13].C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)(Cl)Cl>[CH2:12]([O:14][CH2:15][C:16]1[N:17]([CH2:39][CH2:40][CH3:41])[C:18]2[C:27]3[CH:26]=[C:25]([O:28][CH2:29][CH2:30][CH2:31][N:32]4[CH2:36][CH2:35][CH2:34][C:33]4=[O:37])[CH:24]=[CH:23][C:22]=3[N+:21]([O-:6])=[CH:20][C:19]=2[N:38]=1)[CH3:13]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 70297m-Chloroperbenzoic acidHCID 68972090HCID 68972090, compound

Product 1

HCID 68973272HCID 68973272, compoundYield 69.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

3-Chloroperoxybenzoic acid (50% pure, 1.8 g, 5.26 mmol) was added to a solution of 1-[3-(2-ethoxymethyl-1-propyl-1H-imidazo[4,5-c]quinolin-8-yloxy)propyl]-pyrrolidin-2-one (2.9 g, 5.26 mmol) in chloroform (50 mL). After 30 minutes, saturated aqueous sodium carbonate (20 mL) was added to the solution and the resulting mixture was allowed to stir for 1 hour. The layers were separated and the aqueous layer was extracted with chloroform (3×50 mL). The organic layers were combined, washed with water and saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The crude product was purified by flash chromatography (silica gel, gradient elution with 1-4% methanol in dichloromethane) to yield 1.56 g of 1-(3-{[2-(ethoxymethyl)-5-oxido-1-propyl-1H-imidazo[4,5-c]quinolin-8-yl]oxy}propyl)pyrrolidin-2-one as a tan foam.

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted with chloroform (3×50 mL)
  3. washwashed with water and saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified by flash chromatography (silica gel, gradient elution with 1-4% methanol in dichloromethane)

Sources & evidence

ORD record
ord-2df907dd70d544a4b5b780045c3b8b06
Source dataset
uspto-grants-2014_10
Patent number
US08871782B2

Reaction notes

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