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Sodium Iodide → 1-Phthalimido-4-p-toluenesulfonyl-6,6-difluoro-8-benzyloxy-4-aza-octane

HRID 2072887
ノート
印刷プレビュー

反応式

HRID 2072887 の反応式
[CH2:1]([O:8][CH2:9][CH2:10][C:11]([F:25])([F:24])[CH2:12][NH:13][S:14]([C:17]1[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=1)(=[O:16])=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[K].CC(C)([O-])C.Br[CH2:33][CH2:34][CH2:35][N:36]1[C:40](=[O:41])[C:39]2=[CH:42][CH:43]=[CH:44][CH:45]=[C:38]2[C:37]1=[O:46].[I-].[Na+]>CN(C=O)C.[Cl-].[Na+].O>[C:37]1(=[O:46])[N:36]([CH2:35][CH2:34][CH2:33][N:13]([S:14]([C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=2)(=[O:16])=[O:15])[CH2:12][C:11]([F:25])([F:24])[CH2:10][CH2:9][O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:40](=[O:41])[C:39]2=[CH:42][CH:43]=[CH:44][CH:45]=[C:38]12
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 5238Sodium IodideHCID 21611N-3-BromopropylphthalimideHCID 19860703N-(4-benzyloxy-2,2-difluorobutyl)-p-toluenesulfonamideHCID 50987170Potassium tertbutoxide

生成物 1

HCID 198607071-Phthalimido-4-p-toluenesulfonyl-6,6-difluoro-8-benzyloxy-4-aza-octane

試薬・触媒・溶媒 2

HCID 6228
Dimethylformamide
溶媒
HCID 57417360Sodium chloride; water溶媒

実験手順

To a solution of N-(4-benzyloxy-2,2-difluorobutyl)-p-toluenesulfonamide (7.0 g, 19 mM) in dry DMF (20 mL), is added potassium-tert.-butoxide (2.34 g, 21 mmoles), and the mixture is stirred for 30 minutes. To this mixture are added N-3-bromopropyl-phthalimide (5.1 g, 19 mmoles) and sodium iodide (0.33 g), and the entire mixture is then stirred overnight under nitrogen at room temperature. Following the addition of brine, the mixture is extracted with ether, washed with 1N HCl (twice), then with brine (twice), and dried over Na2SO4. Evaporation of the solvent yields 1-phthalimido-4-p-toluenesulfonyl-6,6-difluoro-8-benzyloxy-4-aza-octane as an oil, which crystallizes on scratching with ether/petroleum ether to form white crytals: 9.5 g (90%).

後処理

  1. stirringthe entire mixture is then stirred overnight under nitrogen at room temperature
  2. extractionthe mixture is extracted with ether
  3. washwashed with 1N HCl (twice), then with brine (twice), and
  4. dry with materialdried over Na2SO4
  5. customEvaporation of the solvent

出典と根拠

ORDレコード
ord-2fc3db3ba2e443a4a4d1dca979f34f88
出典データセット
uspto-grants-1990_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04914240

反応ノート

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