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 1654192ノート

反応式

HRID 1654192 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
55 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-0f25052445a74229a55d7f0ff2791276
出典データセット
uspto-grants-1995_04
特許番号
US05405861

反応ノート

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