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

HRID 232173
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HRID 232173 반응식
[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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 6228
Dimethylformamide
용매
HCID 57417360Sodium chloride; water용매

실험 절차

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 crystals: 9.5 g (90%).

후처리

  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

출처 및 근거

ORD 기록
ord-ad7a92357fe14e3c9023ec6aea014f51
출처 데이터셋
uspto-grants-1989_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04851448

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