p-Toluenesulfonic acid monohydrate → (2R, 3R)-2-(2,4-difluorophenyl)-3-(4-methylenepiperidino)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol p-toluenesulfonate

HRID 53662

反応式

HRID 53662 の反応式
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@@:9]1([CH2:13][N:14]2[CH:18]=[N:17][CH:16]=[N:15]2)[C@H:11]([CH3:12])[O:10]1.O.[C:20]1([CH3:30])[CH:25]=[CH:24][C:23]([S:26]([OH:29])(=[O:28])=O)=[CH:22][CH:21]=1.[CH2:31]=[C:32]1[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]1>C(O)(C)C>[C:20]1([CH3:30])[CH:21]=[CH:22][C:23]([S:26]([O:10][C@@:9]([C:3]2[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=2[F:1])([C@H:11]([N:35]2[CH2:36][CH2:37][C:32](=[CH2:31])[CH2:33][CH2:34]2)[CH3:12])[CH2:13][N:14]2[CH:18]=[N:17][CH:16]=[N:15]2)(=[O:28])=[O:29])=[CH:24][CH:25]=1

参加物

5

反応物 3

HCID 521998p-Toluenesulfonic acid monohydrateHCID 53146584-MethylenepiperidineHCID 101311911-((2-(2,4-Difluorophenyl)-3-methyloxiran-2-yl)methyl)-1H-1,2,4-triazole, (2R-cis)-

生成物 1

HCID 88342129(2R, 3R)-2-(2,4-difluorophenyl)-3-(4-methylenepiperidino)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol p-toluenesulfonate

試薬・触媒・溶媒 1

HCID 3776Isopropanol溶媒

反応条件

温度
90 °C

実験手順

There was dissolved 17.59 g (70 mmol) of (2R,3S)-2-(2,4-difluorophenyl)-3-methyl-2-[(1H-1,2,4-triazole-1-yl)methyl]oxirane in 113 g of an aqueous solution of 4-methylenepiperidine (content: 61%) and the obtained solution was refluxed with heating at 90° C. for 21 hours. After the reaction, an excess of 4-methylenepiperidine was removed under reduced pressure, and the residue was dissolved in 140 ml of isopropyl alcohol and thereto was added 13.32 g (70 mmol) of p-toluenesulfonic acid monohydrate dissolved in 50 ml of isopropyl alcohol. The obtained mixture was allowed to stand for 1 hour at room temperature and overnight in a refrigerator, and then the precipitated crystal was separated by filtration and washed with 50 ml of isopropyl alcohol and dried to obtain 32.20 g of (2R,3R)-2-(2,4-difluorophenyl)-3-(4-methylenepiperidine-1-yl)-1-(1H-1,2,4-triazole-1-yl)butane-2-ol p-toluenesulfonate in a form of a crystal.

後処理

  1. temperaturethe obtained solution was refluxed
  2. customAfter the reaction
  3. customan excess of 4-methylenepiperidine was removed under reduced pressure
  4. dissolutionthe residue was dissolved in 140 ml of isopropyl alcohol
  5. customthe precipitated crystal was separated by filtration
  6. washwashed with 50 ml of isopropyl alcohol
  7. customdried

出典と根拠

ORDレコード
ord-4f8e4265fae44906b5cb69ea516365bb
出典データセット
uspto-grants-1997_04
特許番号
US05620994

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