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 53662노트

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HRID 53662 반응식
[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

참가 물질

5

반응물 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)-

생성물 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

시약·촉매·용매 1

HCID 3776Isopropanol용매

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온도
90 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-4f8e4265fae44906b5cb69ea516365bb
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05620994

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