N-(4-Bromo-2-cyano-5-fluoro-6-hydroxy-3-methylphenyl)-2,2-dimethyl-3-[(phenylmethyl)oxy]propionamide → N-(4-Bromo-2-cyano-5-fluoro-6-hydroxy-3-methylphenyl)-3-hydroxy-2,2-dimethyl-1-propanamide

HRID 17364Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 17364
[Br:1][C:2]1[C:7]([F:8])=[C:6]([OH:9])[C:5]([NH:10][C:11](=[O:24])[C:12]([CH3:23])([CH3:22])[CH2:13][O:14]CC2C=CC=CC=2)=[C:4]([C:25]#[N:26])[C:3]=1[CH3:27].[H][H]>C(OCC)(=O)C>[Br:1][C:2]1[C:7]([F:8])=[C:6]([OH:9])[C:5]([NH:10][C:11](=[O:24])[C:12]([CH3:23])([CH3:22])[CH2:13][OH:14])=[C:4]([C:25]#[N:26])[C:3]=1[CH3:27]

Komponenten

4

Edukt 2

HCID 86630841N-(4-Bromo-2-cyano-5-fluoro-6-hydroxy-3-methylphenyl)-2,2-dimethyl-3-[(phenylmethyl)oxy]propionamideHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 86630842N-(4-Bromo-2-cyano-5-fluoro-6-hydroxy-3-methylphenyl)-3-hydroxy-2,2-dimethyl-1-propanamideAusbeute 50,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

N-(4-Bromo-2-cyano-5-fluoro-6-hydroxy-3-methylphenyl)-2,2-dimethyl-3-[(phenylmethyl)oxy]propionamide (I-105) (5.82 g, 13.37 mmol) was dissolved in ethyl acetate (120 ml), carbon-held palladium catalyst (5% wet, 580 mg) was added, followed by vigorously stirring at room temperature under atmospheric pressure of hydrogen for 18 hours. After the reaction, the insoluble matter was separated by filtration through Celite, the filtrate was concentrated under reduced pressure. The resulting residue was recrystallized and purified with n-hexane/ethyl acetate to obtain the entitled compound (2.32 g, 50%) as a white solid.

Aufarbeitung

  1. additioncarbon-held palladium catalyst (5% wet, 580 mg) was added
  2. customAfter the reaction
  3. customthe insoluble matter was separated by filtration through Celite
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe resulting residue was recrystallized
  6. custompurified with n-hexane/ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-8219cbd171274518809f772ead8ce063
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737166B2

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