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 1654192노트

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HRID 1654192 반응식
[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

참가 물질

4

반응물 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)2회HCID 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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

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온도
55 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-0f25052445a74229a55d7f0ff2791276
출처 데이터셋
uspto-grants-1995_04
특허 번호
US05405861

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