Dimethylformamide → HCID 19860712, compound

HRID 2072890Notes

Reaction equation

HRID 2072890 reaction equation
[C:1]1(=[O:36])[N:5]([CH2:6][CH2:7][CH2:8][N:9]([S:21]([C:24]2[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=2)(=[O:23])=[O:22])[CH2:10][C:11]([F:20])([F:19])[CH2:12]COS(C)(=O)=O)[C:4](=[O:31])[C:3]2=[CH:32][CH:33]=[CH:34][CH:35]=[C:2]12.[C:37]1(=[O:47])[NH:41][C:40](=[O:42])[C:39]2=[CH:43][CH:44]=[CH:45][CH:46]=[C:38]12.[K].[CH3:49]N(C=O)C>O>[C:1]1(=[O:36])[N:5]([CH2:6][CH2:7][CH2:8][N:9]([S:21]([C:24]2[CH:25]=[CH:26][C:27]([CH3:30])=[CH:28][CH:29]=2)(=[O:23])=[O:22])[CH2:10][C:11]([F:20])([F:19])[CH2:12][CH2:49][N:41]2[C:37](=[O:47])[C:38]3=[CH:46][CH:45]=[CH:44][CH:43]=[C:39]3[C:40]2=[O:42])[C:4](=[O:31])[C:3]2=[CH:32][CH:33]=[CH:34][CH:35]=[C:2]12

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 19860695HCID 19860695, compoundHCID 24194345Phthalimide potassium salt

Product 1

HCID 19860712HCID 19860712, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

Under an atmosphere of nitrogen, a mixture of 1-phthalimido-4-p-toluenesulfonyl-6,6-difluoro-8-methanesulfonyloxy-4-aza-octane, (7.6 g, 14 mM), potassium phthalimide (2.85 g, 10% excess) and dry DMF (20 mL) is stirred and heated at 90° C. for 20 hours. Following the addition of water (approximately 100 mL), the reaction is extracted with dichloromethane, washed with 1N KOH (twice), and dried (Na2SO4). The solvents are removed by evaporation to yield and oil (8.7 g) which is flash-chromatographed on silica (300 g, eluent: ethyl acetate/petroleum ether/50--50) with 100 mL fractions being taken. Fractions 15-29 are pooled and the solvent is evaporated to yield 1,8-diphthalimido-4-p-toluenesulfonyl-6,6-difluoro-4-aza-octane, which crystallizes on standing: 6.62 g (80%).

Workup

  1. extractionthe reaction is extracted with dichloromethane
  2. washwashed with 1N KOH (twice), and
  3. dry with materialdried (Na2SO4)
  4. customThe solvents are removed by evaporation
  5. customto yield
  6. customoil (8.7 g) which is flash-chromatographed on silica (300 g, eluent: ethyl acetate/petroleum ether/50--50) with 100 mL fractions
  7. customthe solvent is evaporated

Sources & evidence

ORD record
ord-9f4ec6f9eb564a8b8af074c359a60fdb
Source dataset
uspto-grants-1990_04
Patent number
US04914240

Reaction notes

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