Phosphate → 2-(2,4-Difluorophenyl)-1,2,3-propanetriol

HRID 1003774

Reaction equation

HRID 1003774 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]([OH:20])([CH2:15][O:16]C(=O)C)[CH2:10][O:11]C(=O)C.P([O-])([O-])([O-])=O>C1CCCCC1>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]([OH:20])([CH2:15][OH:16])[CH2:10][OH:11]

Participants

4

Reactant 2

HCID 1061PhosphateHCID 154634621,3-Diacetoxy-2-(2,4-difluorophenyl)-2-propanol

Product 1

HCID 112179522-(2,4-Difluorophenyl)-1,2,3-propanetriolYield 93.2%

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent

Conditions

Temperature
30 °C

Procedure

A 2 l reaction vessel was charged with 10 g of 2-(2,4-difluorophenyl)-1,3-diacetoxy-2-propanol, 2 g of Lipase AP-6 (made by Amano Pharmaceutical Co., Ltd., derived from Aspergillus niger, Enzyme No. 12), 500 ml of 50 mM phosphate buffer (pH 7.0) and 500 ml of cyclohexane. The resulting mixture was stirred at 30° C. for 24 hours. The reaction liquid was extracted three times with 1000 ml of ethyl acetate and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure and the residue was purified by column chromatography on silica gel (n-hexane/ethyl acetate=1/10) to give 6.6 g of 2-(2,4-difluorophenyl)-1,2,3-propanetriol.

Workup

  1. customA 2 l reaction vessel
  2. customThe reaction liquid
  3. extractionwas extracted three times with 1000 ml of ethyl acetate
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was removed under reduced pressure
  6. customthe residue was purified by column chromatography on silica gel (n-hexane/ethyl acetate=1/10)

Sources & evidence

ORD record
ord-80006c0af76c49e9b8b39335b0c8a6a0
Source dataset
uspto-grants-2000_04
Patent number
US06046354

Linked notes

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