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 1846978ノート

反応式

HRID 1846978 の反応式
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]

参加物

4

反応物 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

生成物 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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-fadde94b5eeb4aa5b42a742232527327
出典データセット
uspto-grants-2015_02
特許番号
US08952036B2

反応ノート

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