Methanesulfonyl chloride → (2R,3R)-3-(2,4-difluorophenyl)-3-hydroxy-4-(1H-1,2,4-triazol-1-yl)butan-2-yl methanesulfonate

HRID 273768ノート

反応式

HRID 273768 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:19])([C@H:16]([OH:18])[CH3:17])[CH2:10][N:11]1[CH:15]=[N:14][CH:13]=[N:12]1.[CH3:20][S:21](Cl)(=[O:23])=[O:22]>C(OCC)(=O)C.ClCCl.C(N(CC)CC)C>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@:9]([OH:19])([C@H:16]([O:18][S:21]([CH3:20])(=[O:23])=[O:22])[CH3:17])[CH2:10][N:11]1[CH:15]=[N:14][CH:13]=[N:12]1

参加物

6

反応物 2

HCID 31297Methanesulfonyl chlorideHCID 10286074(2R,3R)-2-(2,4-Difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-2,3-butanediol

生成物 1

HCID 14706441(2R,3R)-3-(2,4-difluorophenyl)-3-hydroxy-4-(1H-1,2,4-triazol-1-yl)butan-2-yl methanesulfonate

試薬・触媒・溶媒 3

HCID 6344Dichloromethane溶媒HCID 8471Triethylamine溶媒HCID 8857Ethyl Acetate溶媒2 回

実験手順

(2R,3R)-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-2,3-butanediol (1.25 g) was dissolved in a mixture of ethyl acetate (40 ml) and dichloromethane (10 ml), to which triethylamine (0.84 ml) and methanesulfonyl chloride (0.48 ml) were added under ice-cooling. The resultant solution was stirred for 30 minutes at room temperature. After adding ethyl acetate, the reaction mixture was washed with water, dried over anhydrous magnesium sulfate and concentrated to obtain (2R,3R)-2-(2,4-difluorophenyl)-3-methanesulfonyloxy-1-(1H-1,2,4-triazol-1-yl)-2-butanol as an oil. Thus obtained compound was dissolved in methanol (40 ml), to which sodium methylate methanolic solution (1.16 ml, 28%) was added under ice-cooling. The resultant solution was stirred for 30 minutes at room temperature. The reaction mixture was concentrated to about 10 ml under reduced pressure, and the residue was extracted with ethyl acetate (100 ml). The ethyl acetate layer was washed with water, dried over anhydrous magnesium sulfate and distilled off the solvent under reduced pressure. The residue was subjected to a silica gel column chromatography (ethyl acetate- dichloromethane=4:l) for purification and then recrystallized from a mixture of ethyl acetate and hexane to give (2R,3S)-2-(2,4-difluorophenyl)-3-methyl-2-[(1H-1,2,4-triazol-1-yl)methyl]oxirane (520 mg) as colorless needles.

後処理

  1. additionwere added under ice-
  2. temperaturecooling
  3. washthe reaction mixture was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-8442e9e3e5574ef3931c57d1580129cb
出典データセット
uspto-grants-1995_02
特許番号
US05387599

反応ノート

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