Ethyl Acetate → HCID 11321729, compound

HRID 1351066Notes

Reaction equation

HRID 1351066 reaction equation
[CH2:1]([O:8][CH:9]([CH3:15])[C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(OCC)(=O)C>P([O-])([O-])([O-])=O>[CH2:1]([O:8][C@H:9]([CH3:15])[C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 8857Ethyl AcetateHCID 561970Ethyl 2-(benzyloxy)propanoate

Product 1

HCID 11321729HCID 11321729, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 1061PhosphateSolvent

Conditions

Temperature
30 °C

Procedure

Ethyl 2-benzyloxypropionate (300 mg) was suspended in 0.1 M phosphate buffer (pH 6.5) (30 mL). “Lipase Fine Grade” (trade name, product of SEIKAGAKU CORPORATION, Rhizopus delemer; 6 mg) was added, followed by stirring at 30° C. for 24 hours. Ethyl acetate was added to the reaction mixture, denatured proteins were removed by filtration through celite. The mixture was adjusted to pH 7.0 with a 1 N aqueous solution of sodium hydroxide, followed by extraction. The organic layer was washed with a 5% aqueous solution of sodium hydrogencarbonate, and then dried over anhydrous sodium sulfate. The solvent was distilled off to afford the title compound as an oil (102 mg, 98.8% ee).

Workup

  1. addition“Lipase Fine Grade” (trade name, product of SEIKAGAKU CORPORATION, Rhizopus delemer; 6 mg) was added
  2. customwere removed by filtration through celite
  3. extractionfollowed by extraction
  4. washThe organic layer was washed with a 5% aqueous solution of sodium hydrogencarbonate
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-1e6b8eb7db12498ab41dcc9a1465c894
Source dataset
uspto-grants-2007_05
Patent number
US07217560B2

Reaction notes

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