Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → (2S,3S)-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)butane-2,3-diol

HRID 1654192Notes

Reaction equation

HRID 1654192 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[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.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>C(O)C>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[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]1

Participants

4

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)2×HCID 14978398(3S)-2-(2,4-difluorophenyl)-3-(3,4,5,6-tetrahydro-2H-pyran-2-yl)oxy-1-(1H-1,2,4-triazol-1-yl)-2-butanol

Product 1

HCID 11054699(2S,3S)-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)butane-2,3-diolYield 35.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
55 °C

Procedure

In ethanol (4 ml) were dissolved (3S)-2-(2,4-difluorophenyl)-3-(3,4,5,6-tetrahydro-2H-pyran-2-yl)oxy-1-(1H-1,2,4-triazol-1-yl)-2-butanol (0.22 g) and pyridinium p-toluenesulfonate (47 mg), which was stirred for two hours at 55° C. To the solution was further added pyridinium p-toluenesulfonate (10 mg), which was stirred for further two hours at 55° C. The reaction mixture was cooled, then the solvent was distilled off. To the residue was added ethyl acetate (30 ml), which was washed with a saturated aqueous sodium chloride solution (10 ml). The ethyl acetate layer was dried over anhydrous magnesium sulfate, then the solvent was distilled off under reduced pressure. To the residue was added ethyl ether, then precipitating crystals were collected by filtration to obtain (2S,3S)-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-2,3-butanediol (60 mg). m.p. 115°-117° C.

Workup

  1. stirringwas stirred for further two hours at 55° C
  2. temperatureThe reaction mixture was cooled
  3. distillationthe solvent was distilled off
  4. additionTo the residue was added ethyl acetate (30 ml), which
  5. washwas washed with a saturated aqueous sodium chloride solution (10 ml)
  6. dry with materialThe ethyl acetate layer was dried over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. additionTo the residue was added ethyl ether
  9. customprecipitating crystals
  10. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-0f25052445a74229a55d7f0ff2791276
Source dataset
uspto-grants-1995_04
Patent number
US05405861

Reaction notes

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