Sodium Sulfite → Ethyl 3-{[(4-{[1-(5-methoxy-3-methyl-1-benzofuran-2-yl)-5-(methylsulfonyl)pentyl]amino}phenyl)carbonyl](methyl)amino}-propanoate

HRID 2091240Notes

Reaction equation

HRID 2091240 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[O:10][C:9]([CH:11]([NH:18][C:19]3[CH:24]=[CH:23][C:22]([C:25]([N:27]([CH3:35])[CH2:28][CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])=[O:26])=[CH:21][CH:20]=3)[CH2:12][CH2:13][CH2:14][CH2:15]SC)=[C:8]([CH3:36])[C:7]=2[CH:37]=1.Cl[C:39]1C=CC=C(C(OO)=O)C=1.[S:49]([O-:52])([O-])=[O:50].[Na+].[Na+]>CC(C)=O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[O:10][C:9]([CH:11]([NH:18][C:19]3[CH:20]=[CH:21][C:22]([C:25]([N:27]([CH3:35])[CH2:28][CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])=[O:26])=[CH:23][CH:24]=3)[CH2:12][CH2:13][CH2:14][CH2:15][S:49]([CH3:39])(=[O:52])=[O:50])=[C:8]([CH3:36])[C:7]=2[CH:37]=1

Participants

5

Reactant 3

HCID 24437Sodium SulfiteHCID 70297m-Chloroperbenzoic acidHCID 66777700Ethyl 3-{[(4-{[1-(5-methoxy-3-methyl-1-benzofuran-2-yl)-5-(methylsulfanyl)pentyl]amino}phenyl)carbonyl](methyl)amino}-propanoate

Product 1

HCID 68627348Ethyl 3-{[(4-{[1-(5-methoxy-3-methyl-1-benzofuran-2-yl)-5-(methylsulfonyl)pentyl]amino}phenyl)carbonyl](methyl)amino}-propanoateYield 37%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution (10 mL) of ethyl 3-{[(4-{[1-(5-methoxy-3-methyl-1-benzofuran-2-yl)-5-(methylsulfanyl)pentyl]amino}phenyl)carbonyl](methyl)amino}-propanoate (263 mg) synthesized in Example A121(1) in acetone was added m-chloroperbenzoic acid (water-containing, purity 69-75%) (344 mg) at 0° C., and the mixture was stirred overnight at room temperature. Saturated aqueous sodium sulfite solution was added to quench the reaction, and the mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (30-70% ethyl acetate/hexane), then by NH silica gel column chromatography (ethyl acetate) to give the title object compound (104 mg, 37%) as a pale-yellow oil.

Workup

  1. customto quench
  2. customthe reaction
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (30-70% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-8292bfb74e8b4c759e5fe545415b9271
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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