Phosphate → 222555-05-7

HRID 351508Notes

Reaction equation

HRID 351508 reaction equation
[CH2:1]([O:3][CH:4]([CH2:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH3:2].P([O-])([O-])([O-])=O>CC(C)=O>[CH2:1]([O:3][C@H:4]([CH2:10][C:11]1[CH:12]=[CH:13][C:14]([OH:17])=[CH:15][CH:16]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH3:2]

Participants

4

Reactant 2

HCID 1061PhosphateHCID 11791243Ethyl 2-ethoxy-3-(4-hydroxyphenyl)propanoate

Product 1

HCID 10220356222555-05-7Yield 82.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Enantiomerically enriched (ee Renantiomer=60%) ethyl 2-ethoxy-3-(4-hydroxyphenyl)propanoate (5.2 g) was dissolved in 30 ml acetone and added to an aqueous 0.1 M phosphate buffer pH 7 (1.0 l). Protease 2A from Aspergillus oryzae (Fluka No: 82463; 0.51 units/mg) (13 g) was added and the mixture was stirred for 3 days at room temperature. The reaction mixture was extracted 4× with 200 ml TBME. After drying of the combined organic phases over Na2SO4and evaporation of the TBME, 4.3 g of ethyl (2R)-2-Ethoxy-3-(4-hydroxyphenyl)propanoate was obtained as an oil (CCE method 2: ee=100%).

Workup

  1. addition0.51 units/mg) (13 g) was added
  2. extractionThe reaction mixture was extracted 4× with 200 ml TBME
  3. dry with materialAfter drying of the combined organic phases over Na2SO4and evaporation of the TBME

Sources & evidence

ORD record
ord-7b800efa21594ed087afb6a664cb8bf1
Source dataset
uspto-grants-2004_06
Patent number
US06743608B2

Reaction notes

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