HCID 605502, compound → HCID 15612355, compound

HRID 2371367Notes

Reaction equation

HRID 2371367 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[C:12](=[O:13])[CH:11](C(OC)=O)[CH:10]2[CH:6]1[CH2:7][C:8](=[O:18])[CH2:9]2)=[O:4]>CO.P([O-])([O-])([O-])=O>[CH3:1][O:2][C:3]([CH:5]1[C:12](=[O:13])[CH2:11][CH:10]2[CH:6]1[CH2:7][C:8](=[O:18])[CH2:9]2)=[O:4]

Participants

4

Reactant 1

HCID 605502HCID 605502, compound

Product 1

HCID 15612355HCID 15612355, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1061PhosphateSolvent

Procedure

One gram of 2,4-bismethoxycarbonylbicyclo[3.3.0]octane-3,7-dione is dissolved in 20 ml of methanol and combined with a solution of 2.5 g of α-chymotrypsin in 150 ml of 0.1-molar phosphate buffer pH 7. The solution is extracted with methyl isobutyl ketone after 22 hours of agitation at 28° C.; the extract is concentrated under vacuum, and the remaining residue is chromatographed over a silica gel column (gradient hexane/ethyl acetate), thus obtaining 610 mg of optically pure 2-methoxycarbonylbicyclo[3.3.0]octane-3,7-dione as an oily liquid.

Workup

  1. extractionThe solution is extracted with methyl isobutyl ketone after 22 hours of agitation at 28° C.
  2. concentrationthe extract is concentrated under vacuum
  3. customthe remaining residue is chromatographed over a silica gel column (gradient hexane/ethyl acetate)

Sources & evidence

ORD record
ord-c9df848a40d0432db9a2709eb5c55621
Source dataset
uspto-grants-1992_03
Patent number
US05093250

Reaction notes

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