p-Toluenesulfonic acid monohydrate → (3S,5S,6R,8S)-8-Allyl-5-(4-chloro-3-fluorophenyl)-6-(3-chlorophenyl)-3-cyclopropyl-8-methyl-2,3,5,6,7,8-hexahydrooxazolo[3,2-a]pyridin-4-ium 4-methylbenzenesulfonate

HRID 1846978노트

반응식

HRID 1846978 반응식
O.[C:2]1([CH3:12])[CH:7]=[CH:6][C:5]([S:8]([OH:11])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH2:13]([C@@:16]1([CH3:44])[CH2:21][C@H:20]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[CH:23]=2)[C@@H:19]([C:29]2[CH:34]=[CH:33][C:32]([Cl:35])=[C:31]([F:36])[CH:30]=2)[N:18]([C@@H:37]([CH:40]2[CH2:42][CH2:41]2)[CH2:38][OH:39])[C:17]1=O)[CH:14]=[CH2:15]>C1(C)C=CC=CC=1>[CH3:12][C:2]1[CH:3]=[CH:4][C:5]([S:8]([O-:11])(=[O:10])=[O:9])=[CH:6][CH:7]=1.[CH2:13]([C@@:16]1([CH3:44])[CH2:21][C@H:20]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[CH:23]=2)[C@@H:19]([C:29]2[CH:34]=[CH:33][C:32]([Cl:35])=[C:31]([F:36])[CH:30]=2)[N+:18]2[C@@H:37]([CH:40]3[CH2:42][CH2:41]3)[CH2:38][O:39][C:17]1=2)[CH:14]=[CH2:15]

참가 물질

4

반응물 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 86731826(3S,5R,6S)-3-Allyl-6-(4-chloro-3-fluorophenyl)-5-(3-chlorophenyl)-1-((S)-1-cyclopropyl-2-hydroxyethyl)-3-methylpiperidin-2-one

생성물 1

HCID 86731827(3S,5S,6R,8S)-8-Allyl-5-(4-chloro-3-fluorophenyl)-6-(3-chlorophenyl)-3-cyclopropyl-8-methyl-2,3,5,6,7,8-hexahydrooxazolo[3,2-a]pyridin-4-ium 4-methylbenzenesulfonate

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

p-Toluenesulfonic acid monohydrate (30.3 g, 159 mmol, Aldrich, St. Louis, Mo.) was added to a solution of (3S,5R,6S)-3-allyl-6-(4-chloro-3-fluorophenyl)-5-(3-chlorophenyl)-1-((S)-1-cyclopropyl-2-hydroxyethyl)-3-methylpiperidin-2-one (73.6 g, 154 mmol) in toluene (386 mL). The reaction mixture was heated at reflux using a Dean-Stark apparatus. After 4 hours, the reaction was cooled and concentrated under reduced pressure to provide the title compound as a pale yellow syrup. The crude product was used in next step without further purification.

후처리

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux
  3. temperaturethe reaction was cooled
  4. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-fadde94b5eeb4aa5b42a742232527327
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08952036B2

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