Phosphate → 2-(2,4-Difluorophenyl)-1,2,3-propanetriol
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
Product 1
Reagents, catalysts & solvents 1
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
- customA 2 l reaction vessel
- customThe reaction liquid
- extractionwas extracted three times with 1000 ml of ethyl acetate
- dry with materialdried over anhydrous sodium sulfate
- customThe solvent was removed under reduced pressure
- customthe residue was purified by column chromatography on silica gel (n-hexane/ethyl acetate=1/10)
Sources & evidence
- ORD record
- ord-81d14d8bbe9243c18a5fa0aa81e11fa0
- Source dataset
- uspto-grants-1997_08
- Patent number
- US05654472
Reaction notes
Loading…