HCID 10401484, compound → 6-(4-Dimethylamino-benzenesulfinyl)-hexanoic acid methyl ester

HRID 2245791Notes

Reaction equation

[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]

Participants

Conditions

Temperature: 60 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record: ord-b8fa0a4d06624f909a9ca580af1f5916
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07683185B2

Reaction notes

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