Sodium Iodide → HCID 54389470, compound

HRID 651255Notes

Reaction equation

HRID 651255 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([N+:12]([O-:14])=[O:13])=[C:6]([CH:8]([OH:11])[CH:9]=[CH2:10])[CH:7]=1.[I-].[Na+].C(=O)([O-])[O-].[K+].[K+].S(C1C=CC(C)=CC=1)(O[CH2:27][CH2:28][CH2:29][NH:30][C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])(=O)=O>CN(C)C=O.C(OCC)(=O)C>[C:34]([O:33][C:31]([NH:30][CH2:29][CH2:28][CH2:27][O:1][C:2]1[CH:3]=[CH:4][C:5]([N+:12]([O-:14])=[O:13])=[C:6]([CH:8]([OH:11])[CH:9]=[CH2:10])[CH:7]=1)=[O:32])([CH3:37])([CH3:36])[CH3:35]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 131203023-[(tert-Butoxycarbonyl)amino]propyl 4-methylbenzene-1-sulfonateHCID 22061198HCID 22061198, compound

Product 1

HCID 54389470HCID 54389470, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

1-(5′-Hydroxy-2′-nitrophenyl)-2-propen-1-ol (2.0 g) is dissolved in dry dimethylformamide (100 ml) and thereto are added sodium iodide (1 equivalent) and potassium carbonate and 3-t-butoxycarbonylaminopropyl tosylate (1.5 equivalent). The mixture is stirred at 50° C. for 6 hours, and thereto is added ethyl acetate. The mixture is washed with an aqueous saturated saline solution, dried over sodium sulfate. After distilling off the solvent, the residue is purified with a silica gel column chromatography to give 1-[5′-(3″-t-butoxycarbonylaminopropyloxy)-2′-nitrophenyl]-2-propen-1-ol (3.53 g) as pale brown caramel.

Workup

  1. washThe mixture is washed with an aqueous saturated saline solution
  2. dry with materialdried over sodium sulfate
  3. distillationAfter distilling off the solvent
  4. customthe residue is purified with a silica gel column chromatography

Sources & evidence

ORD record
ord-1a1a819cce884fe8b5b3701db759e60d
Source dataset
uspto-grants-2001_08
Patent number
US06277992B1

Reaction notes

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