HCID 10879523, compound → HCID 11106580, compound

HRID 849703Notes

Reaction equation

HRID 849703 reaction equation
[C:1]([O:4][CH2:5][CH:6]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:7][O:8]C(=O)C)(=[O:3])[CH3:2]>CC(C)=O.P([O-])([O-])([O-])=O>[C:1]([O:4][CH2:5][C@@H:6]([CH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[CH2:7][OH:8])(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 10879523HCID 10879523, compound

Product 1

HCID 11106580HCID 11106580, compoundYield 38.4%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 1061PhosphateSolvent

Conditions

Temperature
30 °C

Procedure

130 mg of lipase obtained from Pseudomonas fluorescens (Fluka) are added to 0.25 g (1 mmol) of 2-benzyl-1,3-propanediol diacetate (VIII) above dissolved in a mixture of 9.9 ml of acetone and 23.1 ml of phosphate buffer pH=7, and the medium is then heated at 30° C. for 48 hours. The solution is then extracted with ethyl ether (twice 20 ml). The ether phases are combined, dried over magnesium sulphate, filtered and concentrated under vacuum. The residue is purified by chromatography on silica (7/3 ethyl ether/petroleum ether eluent). 80 mg of oil are obtained.

Workup

  1. extractionThe solution is then extracted with ethyl ether (twice 20 ml)
  2. dry with materialdried over magnesium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum
  5. customThe residue is purified by chromatography on silica (7/3 ethyl ether/petroleum ether eluent)

Sources & evidence

ORD record
ord-814eb492d3b04fb49291a84fd833b566
Source dataset
uspto-grants-2000_01
Patent number
US06013829

Reaction notes

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