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tert-Butanol → 7-chloro-5-hydroxymethyl-5-hydroxy-1-[6-(2-methylbenzoylamino)nicotinoyl]-2,3,4,5-tetrahydro-1H-benzazepine

HRID 1440258
ノート
印刷プレビュー

反応式

HRID 1440258 の反応式
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([C:12](=[O:29])[C:13]3[CH:18]=[CH:17][C:16]([NH:19][C:20](=[O:28])[C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[CH3:27])=[N:15][CH:14]=3)[CH2:10][CH2:9]CC(=C)C=2[CH:31]=1.C[N+]1([O-])CC[O:36]CC1.S([O-])(O)=O.[Na+].[C:45]([OH:49])([CH3:48])([CH3:47])[CH3:46]>N1C=CC=CC=1.O.[Os](=O)(=O)(=O)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([C:12](=[O:29])[C:13]3[CH:18]=[CH:17][C:16]([NH:19][C:20](=[O:28])[C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[CH3:27])=[N:15][CH:14]=3)[CH2:10][CH2:9][CH2:47][C:45]([CH2:48][OH:36])([OH:49])[C:46]=2[CH:31]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 6386tert-ButanolHCID 82029Methyl morpholine oxideHCID 229034667-chloro-5-methylidene-1-[6-(2-methylbenzoylamino)nicotinoyl]-2,3,4,5-tetrahydro-1H-benzazepineHCID 23665763Sodium Bisulfite

生成物 1

HCID 229035327-chloro-5-hydroxymethyl-5-hydroxy-1-[6-(2-methylbenzoylamino)nicotinoyl]-2,3,4,5-tetrahydro-1H-benzazepine

試薬・触媒・溶媒 3

HCID 30318Osmium Tetroxide触媒
HCID 962Water溶媒2 回
HCID 1049Pyridine溶媒

実験手順

To a solution of 7-chloro-5-methylidene-1-[6-(2-methylbenzoylamino)nicotinoyl]-2,3,4,5-tetrahydro-1H-benzazepine (0.28 g) in t-butanol (3 ml), pyridine (0.2 ml) and water (1.2 ml) is added 4% aqueous osmium tetraoxide solution (0.2 ml), and further thereto is added 4-methylmorpholine N-oxide (0.1 g). The mixture is refluxed for 5 hours, and cooled. Saturated aqueous sodium hydrogen sulfite solution is added to the reaction mixture, and the mixture is stirred at room temperature for 30 minutes. Water is added to the reaction solution, and the mixture is extracted with a mixture of ethyl acetate and tetrahydrofuran. The extract is washed with water, dried over magnesium sulfate, and evaporated under reduced pressure to remove the solvent. The residue is purified by silica gel column chromatography to give 7-chloro-5-hydroxymethyl-5-hydroxy-1-[6-(2-methylbenzoylamino)nicotinoyl]-2,3,4,5-tetrahydro-1H-benzazepine (0.14 g) as colorless amorphous.

後処理

  1. temperatureThe mixture is refluxed for 5 hours
  2. temperaturecooled
  3. extractionthe mixture is extracted with a mixture of ethyl acetate and tetrahydrofuran
  4. washThe extract is washed with water
  5. dry with materialdried over magnesium sulfate
  6. customevaporated under reduced pressure
  7. customto remove the solvent
  8. customThe residue is purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-f6858c3bd8464d62bd9cdbfa3b446e56
出典データセット
uspto-grants-1996_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05498609

反応ノート

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