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

HRID 2091240ノート

反応式

HRID 2091240 の反応式
[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

参加物

5

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-8292bfb74e8b4c759e5fe545415b9271
出典データセット
uspto-grants-2013_05
特許番号
US08436043B2

反応ノート

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