Sodium Iodide → HCID 13935584, compound

HRID 2072880Notes

Reaction equation

HRID 2072880 reaction equation
[CH2:1]([O:8][CH2:9][C:10]([F:25])([F:24])[CH2:11][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.[I-].[Na+].[CH3:28][C:29](C)([O-])[CH3:30].[K+].BrCCC[C:38]1[CH:48]=[CH:47][CH:46]=[C:40]2[C:41]([NH:43][C:44](=[O:45])[C:39]=12)=[O:42]>CN(C)C=O>[C:41]1(=[O:42])[N:43]([CH2:28][CH2:29][CH2:30][N:13]([S:14]([C:17]2[CH:18]=[CH:19][C:20]([CH3:23])=[CH:21][CH:22]=2)(=[O:16])=[O:15])[CH2:12][CH2:11][C:10]([F:25])([F:24])[CH2:9][O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:44](=[O:45])[C:39]2=[CH:38][CH:48]=[CH:47][CH:46]=[C:40]12

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 13935583HCID 13935583, compoundHCID 21958088BromopropylphthalimideHCID 23665647Potassium tert-butoxide

Product 1

HCID 13935584HCID 13935584, compoundYield 99.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-(4-benzyloxy-3,3-difluorobutyl)-p-toluenesulfonamide (63.17 g, 171.2 mmoles) and sodium iodide (3 g) in dry dimethylformamide (400 mL) is added solid potassium tert.-butoxide (19.2 g, 171 mmoles) with stirring at room temperature. The compound 3-bromopropylphthalimide (46 g, 171 mmoles) is added, and the mixture is stirred at room temperature overnight. The salts are filtered, and the filtrate is evaporated to dryness. The residue is taken up in dichloromethane (500 mL), filtered, and evaporated to dryness. Dissolving in ether (750 mL), washing with aqueous sodium bisulfite (10 g/250 mL), water (3×400 mL), drying (Na2SO4) and evaporation yields 1-phthalimido-4-p-toluenesulfonyl-7,7-difluoro-8-benzyloxy-4-aza-octane as a yellow oil (95.0 g, 99.8%). Traces of ether are removed by stripping twice with chloroform prior to using the material for the next step.

Workup

  1. stirringthe mixture is stirred at room temperature overnight
  2. filtrationThe salts are filtered
  3. customthe filtrate is evaporated to dryness
  4. filtrationfiltered
  5. customevaporated to dryness
  6. dissolutionDissolving in ether (750 mL)
  7. washwashing with aqueous sodium bisulfite (10 g/250 mL), water (3×400 mL)
  8. customdrying
  9. custom(Na2SO4) and evaporation

Sources & evidence

ORD record
ord-d1bd0ff8e4304cbdbed841e09b7caf40
Source dataset
uspto-grants-1990_04
Patent number
US04914240

Reaction notes

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