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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 1489069
ノート
印刷プレビュー

反応式

HRID 1489069 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-144d3a5957344ccf981bd8c7c19f83a3
出典データセット
uspto-grants-1997_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05677299

反応ノート

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