tert-Butyl methyl ether → HCID 86633033, compound

HRID 558058Notes

Reaction equation

HRID 558058 reaction equation
COC(C)(C)C.[C:7]([O:12][CH:13]([O:17][C:18]([CH3:20])=[S:19])[CH2:14][CH2:15][CH3:16])(=[O:11])[CH2:8][CH2:9][CH3:10]>O>[C:7]([O:12][C@@H:13]([O:17][C:18]([CH3:20])=[S:19])[CH2:14][CH2:15][CH3:16])(=[O:11])[CH2:8][CH2:9][CH3:10]

Participants

4

Reactant 2

HCID 15413tert-Butyl methyl etherHCID 86633034HCID 86633034, compound

Product 1

HCID 86633033HCID 86633033, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 33 mL methyl-tert-butyl ether (MTBE) and 0.33 mL water was stirred until a clear solution was obtained (ca. 5 hrs). To this solution was added methylthiocarbonyloxybutyl butanoate (2e) (2.0 g) and PLE/MPEG (60 mg/1 g; 12.65 g). The resulting suspension was stirred at room temperature. The reaction was monitored by 1H-NMR using a chiral solvating agent. After ca. 5 days, the reaction was quenched by filtration through a pad of CELITE® 545. The supernatant was washed with water, aqueous sodium bicarbonate (NaHCO3) and brine, and dried over anhydrous sodium sulfate (Na2SO4). Evaporation of the solvent afforded 0.20 g (20% yield) of the title compound (16). The enantiomeric excess as determined by chiral HPLC was 90% e.e.

Workup

  1. customwas obtained (ca. 5 hrs)
  2. stirringThe resulting suspension was stirred at room temperature
  3. customthe reaction was quenched by filtration through a pad of CELITE® 545
  4. washThe supernatant was washed with water, aqueous sodium bicarbonate (NaHCO3) and brine
  5. dry with materialdried over anhydrous sodium sulfate (Na2SO4)
  6. customEvaporation of the solvent

Sources & evidence

ORD record
ord-cc80f7fc8ba440c3961ce5398493a1b0
Source dataset
uspto-grants-2011_11
Patent number
US08062870B2

Reaction notes

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