Phosphate → HCID 58916976, compound

HRID 1362845Notes

Reaction equation

HRID 1362845 reaction equation
P([O-])([O-])([O-])=O.[CH3:6][O:7][C:8](=[O:24])[C:9]([CH2:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=1)([CH3:14])[C:10]([O:12]C)=[O:11]>C(O)(C)C>[CH3:6][O:7][C:8](=[O:24])[C:9]([CH2:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=1)([CH3:14])[C:10]([OH:12])=[O:11]

Participants

4

Reactant 2

HCID 1061PhosphateHCID 66921686HCID 66921686, compound

Product 1

HCID 58916976HCID 58916976, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

300 ml Phosphate buffer are heated to 30° C. and 124 mg of pig liver esterase are added and left for 15 minutes 3 g of 2-(4-chlor-phenoxy-methyl)-2-methyl-malonic acid dimethyl ester in 10 ml of isopropanol the mixture is stirred at +30° C. for 17 hours. The reaction mixture is extracted with ethylacetate to remove neutral organic matter, the remaining solution acidified to pH 2 with 2N hydrogenchlorid and extracted again with ethylacetate. The organic extract is dried over sodium sulfate, the solvent evaporated and the residue chromatographed (RP-18 column, eluant: acetonitril/water 1:1). Yield 1.73 g, M.p. 93° C.

Workup

  1. addition124 mg of pig liver esterase are added
  2. extractionThe reaction mixture is extracted with ethylacetate
  3. customto remove neutral organic matter
  4. extractionextracted again with ethylacetate
  5. extractionThe organic extract
  6. dry with materialis dried over sodium sulfate
  7. customthe solvent evaporated
  8. customthe residue chromatographed (RP-18 column, eluant: acetonitril/water 1:1)

Sources & evidence

ORD record
ord-25c8c0d7f4af4338b827259990b8fa31
Source dataset
uspto-grants-2011_02
Patent number
US07884103B2

Reaction notes

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