Sodium Iodide → HCID 12074070, compound

HRID 413923Notes

Reaction equation

HRID 413923 reaction equation
[CH2:1]([O:3][CH2:4][O:5][CH2:6][C@@H:7]([NH:13][C:14]([C:16]1[CH:21]=[CH:20][C:19]([I:22])=[CH:18][CH:17]=1)=[O:15])[CH2:8][CH2:9][C:10]([OH:12])=[O:11])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].[CH2:31](Br)[CH:32]=[CH2:33]>CN(C)C=O>[CH2:33]([O:11][C:10](=[O:12])[CH2:9][CH2:8][C@H:7]([NH:13][C:14]([C:16]1[CH:21]=[CH:20][C:19]([I:22])=[CH:18][CH:17]=1)=[O:15])[CH2:6][O:5][CH2:4][O:3][CH2:1][CH3:2])[CH:32]=[CH2:31]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 12074069HCID 12074069, compound

Product 1

HCID 12074070HCID 12074070, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the compound prepared in Example 2 (4.11 g) in dimethylformamide (DMF; 20 ml), potassium carbonate (1.62 g), sodium iodide (small amount) and allyl bromide (5 ml) were added. The mixture was vigorously stirred overnight. The reaction mixture was extracted with ethyl acetate, dried over anhydrous magnesium sulfate and concentrated. The residue was washed with hexane to give the title compound having the following physical data.

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated
  4. washThe residue was washed with hexane

Sources & evidence

ORD record
ord-f1b415c153e14d06923f72ed0f5f6276
Source dataset
uspto-grants-2003_05
Patent number
US06569899B1

Reaction notes

Loading…