Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → (2R,3R)-2-(2,5-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)butane-2,3-diol
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9]([OH:25])([C@H:16]([O:18]C1CCCCO1)[CH3:17])[CH2:10][N:11]1[CH:15]=[N:14][CH:13]=[N:12]1.CC1C=CC(S([O-])(=O)=O)=CC=1.C1C=C[NH+]=CC=1>CCO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C@:9]([OH:25])([C@H:16]([OH:18])[CH3:17])[CH2:10][N:11]1[CH:15]=[N:14][CH:13]=[N:12]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 55 °C
Procedure
A mixture of (3R)-2-(2,5-difluorophenyl)-3-(3,4,5,6-tetrahydro-2H-pyran-2-yloxy)-1-(1H-1,2,4-triazol-1-yl)-2-butanol (43.9 g, 0.124 mol) and PPTS (15.6 g, 62.1 mmol) in EtOH ( 400 ml ) was stirred at 55° C. for 5 hrs. The mixture was was evaporated to remove solvent down to 100 ml. The residue was poured into ice-aqueous NaHCO3 (500 ml). The whole was extracted with EtOAc (400 ml+200 ml×2). The combined organic layer was dried over Na2SO4 and concentrated in vacuo. The residue was chromatographed on silicagel (CH2Cl2: MeOH=20:1) to give (2R,3R)-2-(2,5-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-2,3-butanediol (18.0 g, 54%).
Workup
- customThe mixture was was evaporated
- customto remove solvent down to 100 ml
- additionThe residue was poured into ice-aqueous NaHCO3 (500 ml)
- extractionThe whole was extracted with EtOAc (400 ml+200 ml×2)
- dry with materialThe combined organic layer was dried over Na2SO4
- concentrationconcentrated in vacuo
- customThe residue was chromatographed on silicagel (CH2Cl2: MeOH=20:1)
Sources & evidence
- ORD record
- ord-2799463361c24aec90cb4fc5d7182a3d
- Source dataset
- uspto-grants-2001_10
- Patent number
- US06300353B1
Reaction notes
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