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

HRID 2245792Notes

Reaction equation

HRID 2245792 reaction equation
[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]

Participants

7

Reactant 2

HCID 10408174HCID 10408174, compoundHCID 23667635Sodium periodate

Product 1

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

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

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%).

Workup

  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)

Sources & evidence

ORD record
ord-3a7a0ed2618b4b108efc7d859b0d2c32
Source dataset
uspto-grants-2010_03
Patent number
US07683185B2

Reaction notes

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