HCID 54389470, compound → HCID 54245016, compound

HRID 651256Notes

Reaction equation

HRID 651256 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:14]=[CH:15][C:16]([N+:23]([O-:25])=[O:24])=[C:17]([CH:19]([OH:22])[CH:20]=[CH2:21])[CH:18]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(Cl)(Cl)Cl.[O-2].[O-2].[Mn+4]>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:14]=[CH:15][C:16]([N+:23]([O-:25])=[O:24])=[C:17]([C:19](=[O:22])[CH:20]=[CH2:21])[CH:18]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 1

HCID 54389470HCID 54389470, compound

Product 1

HCID 54245016HCID 54245016, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6212ChloroformSolvent

Procedure

1-(5′-(3″-t-butoxycarbonylaminopropyloxy)-2′-nitrophenyl)-2-propen-1-ol (9.66 g) is dissolved in chloroform (300 ml) and thereto is added activated manganese dioxide (7.2 g), and the mixture is heated with reflux. After completion of the reaction, inorganic materials are filtered off with celite, and the filtrate is concentrated, and thereto is added ethyl acetate. The organic layer is separated, 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-one (6.01 g) as yellow color crystal. m.p.: 65-71° C.

Workup

  1. temperaturethe mixture is heated
  2. temperaturewith reflux
  3. customAfter completion of the reaction, inorganic materials
  4. filtrationare filtered off with celite
  5. concentrationthe filtrate is concentrated
  6. additionis added ethyl acetate
  7. customThe organic layer is separated
  8. washwashed with an aqueous saturated saline solution
  9. dry with materialdried over sodium sulfate
  10. distillationAfter distilling off the solvent
  11. customthe residue is purified with a silica gel column chromatography

Sources & evidence

ORD record
ord-4b795dc675a24d719764e0bb5fb762f3
Source dataset
uspto-grants-2001_08
Patent number
US06277992B1

Reaction notes

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