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

HRID 232173Notes

Reaction equation

HRID 232173 reaction equation
[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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-ad7a92357fe14e3c9023ec6aea014f51
Source dataset
uspto-grants-1989_07
Patent number
US04851448

Reaction notes

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