Water → HCID 86633035, compound

Participants

Reaction Steps

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.

Provenance & Evidence