Sodium Iodide → HCID 12074070, compound

HRID 583944Notes

Reaction equation

HRID 583944 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-73a17c3ebe9c405fa72a5c05403f7bec
Source dataset
uspto-grants-2005_08
Patent number
US06924307B2

Reaction notes

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