4-hydroxy-3-methoxy-N-[3-(2-phenylethynyl)phenyl]-phenylacetamide → 4-hydroxy-3-methoxy-N-[3-[(Z)-2-phenylvinyl]phenyl]-phenylacetamide

HRID 7069

Reaktionsgleichung

Reaktionsgleichung von HRID 7069
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]#[C:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:13]=2)=[O:10])=[CH:4][C:3]=1[O:26][CH3:27]>C(OCC)(=O)C.[Pd].CC([O-])=O.CC([O-])=O.[Pb+2]>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14](/[CH:18]=[CH:19]\[C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH:13]=2)=[O:10])=[CH:4][C:3]=1[O:26][CH3:27]

Komponenten

4

Edukt 1

HCID 220196124-hydroxy-3-methoxy-N-[3-(2-phenylethynyl)phenyl]-phenylacetamide

Produkt 1

HCID 586798714-hydroxy-3-methoxy-N-[3-[(Z)-2-phenylvinyl]phenyl]-phenylacetamideAusbeute 33,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 131709914Lindlars catalystKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

4-Hydroxy-3-methoxy-N-[3-(2-phenylethynyl)phenyl]phenylacetamide (150 mg) obtained in Example 36 is dissolved in ethyl acetate (10 ml), and thereto is added Lindlar catalyst (5% lead-poisoned palladium-calcium carbonate) (15 mg), and the mixture is subjected to catalytic hydrogenation at 25° C. The catalyst is removed by filtration, and the solvent is evaporated under reduced pressure. The residue is purified by silica gel column chromatography (eluent: gradient from 0% to 100% hexane/ethyl acetate) to give the desired compound (50 mg).

Aufarbeitung

  1. customis subjected to catalytic hydrogenation at 25° C
  2. customThe catalyst is removed by filtration
  3. customthe solvent is evaporated under reduced pressure
  4. customThe residue is purified by silica gel column chromatography (eluent: gradient from 0% to 100% hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-07dd7afb520a43b7959c4a57316588b6
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07084176B2

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