Phosphate → HCID 86630302, compound

HRID 1158247Notes

Reaction equation

HRID 1158247 reaction equation
P([O-])([O-])([O-])=O.[CH2:6]([N:9]1[CH:13]([CH2:14][CH2:15][CH3:16])[CH2:12][O:11][S@@:10]1=[O:17])[CH2:7][CH3:8].I([O-])(=O)(=O)=[O:19].[Na+]>C(OCC)(=O)C.O.[Ru](=O)=O>[CH2:6]([N:9]1[C@@H:13]([CH2:14][CH2:15][CH3:16])[CH2:12][O:11][S:10]1(=[O:19])=[O:17])[CH2:7][CH3:8]

Participants

6

Reactant 3

HCID 1061PhosphateHCID 23667635Sodium periodateHCID 67426478HCID 67426478, compound

Product 1

HCID 86630302HCID 86630302, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 16211523Ruthenium dioxide hydrateCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Ruthenium dioxide hydrate (3 mg) and a phosphate buffer solution (pH 7.4, 28.7 mL) were subsequently added to a solution of (S)-3,4-dipropyl-1,2,3-oxathiazolidine 2-oxide (5.74 g) in ethyl acetate (46 mL) under ice-cooling and stirring. Sodium periodate (7.06 g) was added to the solution under ice-cooling and stirring, and then vigorously stirred at room temperature for 30 minutes. The suspension was filtered, and the insoluble matter was washed with ethyl acetate (17 mL). The filtrate and the washings were combined. The organic layer was separated and washed subsequently with a saturated aqueous sodium hydrogen carbonate solution (11.5 mL), an aqueous 10% sodium thiosulfate solution (11.5 mL) and a saturated aqueous sodium chloride solution (11.5 mL). Anhydrous sodium sulfate and activated carbon (0.57 g) were added to the organic layer and stirred at room temperature for 1 hour. The suspension was filtered, and the filtrate was concentrated under reduced pressure. The residue was added with tetrahydrofuran (8.6 mL) and concentrated under reduced pressure at 40° C. or lower to give (S)-3,4-dipropyl-1,2,3-oxathiazolidine 2,2-dioxide (5.83 g, 94% yield) as an orange-brown oil.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. stirringstirring
  4. stirringvigorously stirred at room temperature for 30 minutes
  5. filtrationThe suspension was filtered
  6. washthe insoluble matter was washed with ethyl acetate (17 mL)
  7. customThe organic layer was separated
  8. washwashed subsequently with a saturated aqueous sodium hydrogen carbonate solution (11.5 mL)
  9. additionAnhydrous sodium sulfate and activated carbon (0.57 g) were added to the organic layer
  10. stirringstirred at room temperature for 1 hour
  11. filtrationThe suspension was filtered
  12. concentrationthe filtrate was concentrated under reduced pressure
  13. additionThe residue was added with tetrahydrofuran (8.6 mL)
  14. concentrationconcentrated under reduced pressure at 40° C.

Sources & evidence

ORD record
ord-ac366e2d34f94b6aafa13a15a28b494b
Source dataset
uspto-grants-2010_10
Patent number
US07807840B2

Reaction notes

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