m-Chloroperbenzoic acid → HCID 86594227, compound

HRID 1373932Notes

Reaction equation

HRID 1373932 reaction equation
[CH2:1]([O:3][CH2:4][C:5]1[N:6]([NH:18][CH2:19][CH2:20][CH2:21][NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[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)[CH3:2].C1C=C(Cl)C=C(C(OO)=[O:38])C=1>C(Cl)(Cl)Cl.C([O-])([O-])=O.[Na+].[Na+]>[CH2:1]([O:3][CH2:4][C:5]1[N:6]([NH:18][CH2:19][CH2:20][CH2:21][NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[C:7]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N+:10]([O-:38])=[CH:9][C:8]=2[N:17]=1)[CH3:2]

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 86594226HCID 86594226, compound

Product 1

HCID 86594227HCID 86594227, compoundYield 99.9%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolvent2×HCID 10340Sodium CarbonateSolvent

Procedure

A solution of tert-butyl {3-[(2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)amino]propyl}carbamate (1.34 g, 3.35 mmol) in 30 mL of CHCl3 was treated with MCPBA (1.45 g, 5.03 mmol, 77% max). After 3 h, the reaction mixture was diluted with 10% Na2CO3 solution and CHCl3 and the phases were separated. The organic portion was washed with water and brine, dried over Na2SO4, filtered and concentrated under reduced pressure to yield tert-butyl {3-[(2-ethoxymethyl-5-oxido-1H-imidazo[4,5-c]quinolin-1-yl)amino]propyl}carbamate (1.39 g) as an orange foam.

Workup

  1. customthe phases were separated
  2. washThe organic portion was washed with water and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-50a56cf31b2a4bfcbd402a6000fcf9c0
Source dataset
uspto-grants-2007_01
Patent number
US07163947B2

Reaction notes

Loading…