Sodium Iodide → HCID 12148452, compound

HRID 457264Notes

Reaction equation

HRID 457264 reaction equation
[C:1]([C:3]1[CH:26]=[CH:25][C:6]([NH:7][C:8]2[C:9]([OH:24])([CH3:23])[CH:10](S([O-])(=O)=O)C=C(CCC=O)C=2C)=[CH:5][C:4]=1[C:27]([F:30])([F:29])[F:28])#[N:2].[I-:31].[Na+].C(OCC)(=[O:35])C>CC(C)=O>[C:1]([C:3]1[CH:26]=[CH:25][C:6]([NH:7][C:8](=[O:35])[C:9]([OH:24])([CH3:23])[CH2:10][I:31])=[CH:5][C:4]=1[C:27]([F:30])([F:29])[F:28])#[N:2]

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 8857Ethyl AcetateHCID 131724647HCID 131724647, compound

Product 1

HCID 12148452HCID 12148452, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

In a 50 ml flask, equipped with a magnetic stirrer, 0.135 g of the tosylate compound of Example 12 was treated with an excess of sodium iodide (>10 equivalents) in 10 ml of acetone at reflux for 48 hours. After cooling to room temperature, the reaction mixture was transferred to a separation funnel and 20 ml of ethyl acetate was added. The organic layer was washed with 20 ml of water, 20 ml of 0.5M aqueous Na2S2O3, and 20 ml of brine, dried (Na2SO4) and concentrated at reduced pressure. The crude product was purified by column chromatography (Merck 60 SiO2, eluens ethyl acetate/heptane=3/2) to give two fractions. The first fraction was the product as was determined by 1H-NMR spectroscopy. Isolated yield: 0.048 g (40%).

Workup

  1. customIn a 50 ml flask, equipped with a magnetic stirrer
  2. temperatureat reflux for 48 hours
  3. customthe reaction mixture was transferred to a separation funnel
  4. washThe organic layer was washed with 20 ml of water, 20 ml of 0.5M aqueous Na2S2O3, and 20 ml of brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated at reduced pressure
  7. customThe crude product was purified by column chromatography (Merck 60 SiO2, eluens ethyl acetate/heptane=3/2)
  8. customto give two fractions
  9. customIsolated yield: 0.048 g (40%)

Sources & evidence

ORD record
ord-7f497435cf2c40edb16b3d59946cc3e5
Source dataset
uspto-grants-2007_03
Patent number
US07186854B2

Reaction notes

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