Sodium Iodide → HCID 54389470, compound

HRID 356576Notes

Reaction equation

HRID 356576 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=O)C.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 DMF (100 ml) and thereto are added sodium iodide (1 equivalent), 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 a saturated sodium chloride solution and dried over sodium sulfate. The residue is purified by silica gel column chromatography to give 1-[5'-(3"-t-butoxycarbonylaminopropyloxy)-2'-nitrophenyl]-2-propen-1-ol (3.53 g) as a pale brown caramel.

Workup

  1. washThe mixture is washed with a saturated sodium chloride solution
  2. dry with materialdried over sodium sulfate
  3. customThe residue is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-b5ea5783f30b41f8a49fd844e11c69ee
Source dataset
uspto-grants-1998_11
Patent number
US05837673

Reaction notes

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