Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → (2R,3R)-2-(2,4-Difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-2,3-butanediol

HRID 1654200ノート

反応式

HRID 1654200 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 14978397(3R)-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 10286074(2R,3R)-2-(2,4-Difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-2,3-butanediol収率 40.9%

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 (50 ml) were dissolved (3R)-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 (4.4 g) and pyridinium p-toluenesulfonate (0.93 g). The solution was stirred for two hours at 55° C. to which was further added pyridinium p-toluenesulfonate (0.20 g), followed by stirring 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 (250 ml), which was washed with water (50 ml) and a saturated aqueous solution of sodium chloride (50 ml) successively. 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 give (2R,3R)-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-2,3-butanediol (1.37 g). m.p. 115°-117° C. [α]D =-80.3° C. (c=1.0 in methanol)

後処理

  1. stirringby stirring 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 (250 ml), which
  5. washwas washed with water (50 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-508de310a21142f2845a92e491210f38
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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