Water → HCID 86633035, compound

HRID 558059Notes

Reaction equation

HRID 558059 reaction equation
COC(C)(C)C.O.[C:8]([O:11][CH:12]([O:16][C:17]([CH3:19])=[S:18])[CH:13]([CH3:15])[CH3:14])(=[O:10])[CH3:9]>CCCCCC>[C:8]([O:11][C@@H:12]([O:16][C:17]([CH3:19])=[S:18])[CH:13]([CH3:15])[CH3:14])(=[O:10])[CH3:9]

Participants

5

Reactant 3

HCID 962WaterHCID 15413tert-Butyl methyl etherHCID 86633036HCID 86633036, compound

Product 1

HCID 86633035HCID 86633035, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

Twenty (20) mL of methyl-tert-butyl ether (MTBE) and 0.2 mL of water were shaken for 4 hrs until the solution was clear at which time 1 g of 2-methyl-1-methylthiocarbonyloxypropyl acetate (2f) was added, followed by 1.32 g of PLE/MPEG (60 mg/1 g). The mixture was shaken on an orbital shaker for 7 hrs. Hexane was added and the mixture was filtered through CELITE® 545 pad. The organic solution was washed with water, aqueous sodium bicarbonate (NaHCO3) solution and brine, and dried over anhydrous sodium sulfate (Na2SO4). After evaporation of solvent, 0.32 g (64% yield) of the title compound (17) was obtained having an enantiomeric excess of 64% e.e. The absolute configuration was determined by independent stereospecific synthesis and by derivatization to a compound having known stereochemistry.

Workup

  1. additionwas added
  2. filtrationthe mixture was filtered through CELITE® 545 pad
  3. washThe organic solution was washed with water, aqueous sodium bicarbonate (NaHCO3) solution and brine
  4. dry with materialdried over anhydrous sodium sulfate (Na2SO4)
  5. customAfter evaporation of solvent

Sources & evidence

ORD record
ord-5eb1c196a20a44348677e0dcede3f00e
Source dataset
uspto-grants-2011_11
Patent number
US08062870B2

Reaction notes

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