HCID 10408174, Verbindung → 6-(4-((4-Chlorobenzyl)-methylamino)-benzenesulfinyl)-hexanoic acid methyl ester

HRID 2245792Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2245792
[CH3:1][O:2][C:3](=[O:26])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][S:9][C:10]1[CH:15]=[CH:14][C:13]([N:16]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=2)[CH3:17])=[CH:12][CH:11]=1.I([O-])(=O)(=O)=[O:28].[Na+]>CO.O1CCCC1.O.C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:26])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][S:9]([C:10]1[CH:15]=[CH:14][C:13]([N:16]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=2)[CH3:17])=[CH:12][CH:11]=1)=[O:28]

Komponenten

7

Edukt 2

HCID 10408174HCID 10408174, VerbindungHCID 23667635Sodium periodate

Produkt 1

HCID 100470066-(4-((4-Chlorobenzyl)-methylamino)-benzenesulfinyl)-hexanoic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 6-(4-((4-chlorobenzyl)-methylamino)-phenylsulfanyl)-hexanoic acid methyl ester (840 mg, 2.1 mmol) in methanol (60 mL) and tetrahydrofuran (30 mL) was added dropwise at 0° C. a solution of sodium metaperiodate (504 mg, 2.3 mmol) in distilled water (20 mL). The mixture was heated at reflux for 1 hour. The solution was concentrated under reduced pressure to give an oil that was dissolved in ethyl acetate (75 mL). The organic layer was washed with saturated aqueous sodium hydrogen carbonate (50 mL), distilled water (50 mL), and brine (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 (50:50:1 ethyl acetate:40-60° C. ether:triethylamine). The title compound was obtained as a colourless oil (759 mg, 87%).

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 1 hour
  3. concentrationThe solution was concentrated under reduced pressure
  4. customto give an oil that
  5. washThe organic layer was washed with saturated aqueous sodium hydrogen carbonate (50 mL)
  6. distillationdistilled water (50 mL), and brine (50 mL)
  7. dry with materialThe organic layer was dried over anhydrous MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customto give an oil that
  11. customwas purified by flash chromatography (50:50:1 ethyl acetate:40-60° C. ether:triethylamine)

Quellen und Nachweise

ORD-Eintrag
ord-3a7a0ed2618b4b108efc7d859b0d2c32
Quelldatensatz
uspto-grants-2010_03
Patentnummer
US07683185B2

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