Phosphate → HCID 86633029, compound

HRID 558055Notes

Reaction equation

HRID 558055 reaction equation
[C:1]([O:6][CH:7]([O:11][C:12]([CH3:14])=[S:13])[CH:8]([CH3:10])[CH3:9])(=[O:5])[CH2:2][CH2:3][CH3:4].P([O-])([O-])([O-])=O>C(OC(C)C)(C)C.CCOCC>[C:1]([O:6][C@H:7]([O:11][C:12]([CH3:14])=[S:13])[CH:8]([CH3:10])[CH3:9])(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 2

HCID 1061PhosphateHCID 86633030HCID 86633030, compound

Product 1

HCID 86633029HCID 86633029, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 7914Diisopropyl EtherSolvent

Procedure

To a solution of 2-methyl-1-methylthiocarbonyloxypropyl butanoate (2d) (0.5 g) in 2 mL of diisopropyl ether, 0.025 g of lipase from Candida rugosa was added, followed by 10 mL of phosphate buffer. The mixture was stirred at room temperature for ca. 24 hrs. The reaction mixture was diluted with ether and the organic solution filtered through a pad of CELITE® 545. The ether solution was washed with water (2 times) and brine, and dried over anhydrous sodium sulfate (Na2SO4). The solvent was evaporated under reduced pressure to provide 0.16 g (64% yield) of the title compound (7). 1H-NMR using a chiral solvating agent showed a single isomer and the absolute configuration was confirmed by derivatization to a compound having a known stereochemistry.

Workup

  1. filtrationthe organic solution filtered through a pad of CELITE® 545
  2. washThe ether solution was washed with water (2 times) and brine
  3. dry with materialdried over anhydrous sodium sulfate (Na2SO4)
  4. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-776879f20c3a4868ba4db6db35255ad2
Source dataset
uspto-grants-2011_11
Patent number
US08062870B2

Reaction notes

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