HCID 10401484、化合物 → 6-(4-Dimethylamino-benzenesulfinyl)-hexanoic acid methyl ester

HRID 2245791ノート

反応式

HRID 2245791 の反応式
[CH3:1][O:2][C:3](=[O:19])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][S:9][C:10]1[CH:15]=[CH:14][C:13]([N:16]([CH3:18])[CH3:17])=[CH:12][CH:11]=1.I([O-])(=O)(=O)=[O:21].[Na+]>CO.O.C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:19])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][S:9]([C:10]1[CH:11]=[CH:12][C:13]([N:16]([CH3:18])[CH3:17])=[CH:14][CH:15]=1)=[O:21]

参加物

6

反応物 2

HCID 10401484HCID 10401484、化合物HCID 23667635Sodium periodate

生成物 1

HCID 100175446-(4-Dimethylamino-benzenesulfinyl)-hexanoic acid methyl ester収率 81%

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
60 °C

実験手順

To a solution of 6-(4-dimethylamino-phenylsulfanyl)-hexanoic acid methyl ester (1.4 g, 5.0 mmol) in methanol (60 mL) was added dropwise at 0° C. a solution of sodium metaperiodate (1.3 g, 6.0 mmol) in distilled water (20 mL). The mixture was heated at 60° C. for 1 hour. The solution was concentrated under reduced pressure to give an oil that was dissolved in ethyl acetate (150 mL). The organic layer was washed with saturated aqueous sodium hydrogen carbonate (100 mL), distilled water (2×50 mL), and lastly with brine (2×50 mL). The organic layer was dried over anhydrous MgSO4, filtered and concentrated under reduced pressure to give an oil that was purified by flash chromatography (100:1 ethyl acetate:triethylamine) to give the title compound (1.2 g, 81%) as a colourless oil.

後処理

  1. concentrationThe solution was concentrated under reduced pressure
  2. customto give an oil that
  3. washThe organic layer was washed with saturated aqueous sodium hydrogen carbonate (100 mL)
  4. distillationdistilled water (2×50 mL)
  5. dry with materialThe organic layer was dried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto give an oil that
  9. customwas purified by flash chromatography (100:1 ethyl acetate:triethylamine)

出典と根拠

ORDレコード
ord-b8fa0a4d06624f909a9ca580af1f5916
出典データセット
uspto-grants-2010_03
特許番号
US07683185B2

反応ノート

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