Water → HCID 67426478, compound

HRID 1925484Notes

Reaction equation

HRID 1925484 reaction equation
CN1CCOCC1.[CH2:8]([NH:11][C@H:12]([CH2:16][OH:17])[CH2:13][CH2:14][CH3:15])[CH2:9][CH3:10].[S:18](Cl)(Cl)=[O:19].O>ClCCl>[CH2:8]([N:11]1[CH:12]([CH2:13][CH2:14][CH3:15])[CH2:16][O:17][S@@:18]1=[O:19])[CH2:9][CH3:10]

Participants

6

Reactant 4

HCID 962WaterHCID 79724-MethylmorpholineHCID 24386Thionyl ChlorideHCID 55300429(2S)-2-(Propylamino)pentan-1-ol

Product 1

HCID 67426478HCID 67426478, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

N-Methylmorpholine (27.3 mL) was added to a solution of (S)—N-propylnorvalinol (11.5 g) in dichloromethane (200 mL) under stirring at room temperature. A solution of thionyl chloride (9.32 mL) in dichloromethane (64 mL) was added dropwise to the resulting light yellow solution under ice-cooling and stirring. The resulting suspension was stirred at room temperature. Water was added to the suspension under ice-cooling and stirring, and the mixture was extracted with dichloromethane. The organic layer was washed with an aqueous 1 mol/L hydrochloric acid solution and subsequently with a saturated aqueous sodium hydrogen carbonate solution, dried over anhydrous magnesium sulfate, and then the solvent was removed by distillation under reduced pressure. The residue was dried under reduced pressure at room temperature overnight to give (S)-3,4-dipropyl-1,2,3-oxathiazolidine 2-oxide as a colorless oil (16.1 g, 79% yield, cis:trans=about 38:62 determined from the integration ratio in 1H-NMR).

Workup

  1. temperaturecooling
  2. stirringstirring
  3. stirringThe resulting suspension was stirred at room temperature
  4. temperaturecooling
  5. stirringstirring
  6. extractionthe mixture was extracted with dichloromethane
  7. washThe organic layer was washed with an aqueous 1 mol/L hydrochloric acid solution and subsequently with a saturated aqueous sodium hydrogen carbonate solution
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customthe solvent was removed by distillation under reduced pressure
  10. customThe residue was dried under reduced pressure at room temperature overnight

Sources & evidence

ORD record
ord-0569eb3e54774f43bb5e3b01dec721e3
Source dataset
uspto-grants-2012_05
Patent number
US08178686B2

Reaction notes

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