N-Acetyl-L-phenylalanine → 2-Acetamidocinnamic acid

HRID 329796

Reaktionsgleichung

Reaktionsgleichung von HRID 329796
C(N[C@H:5]([C:13]([OH:15])=[O:14])[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)(=O)C.[CH3:16][C:17]1[O:18]C(=O)C(=CC2C=CC=CC=2)[N:21]=1>O>[NH:21]([C:12]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH:6]=[CH:5][C:13]([OH:15])=[O:14])[C:17]([CH3:16])=[O:18]

Komponenten

4

Edukt 2

HCID 74839N-Acetyl-L-phenylalanineHCID 949464-benzylidene-2-methyl-4H-oxazol-5-one

Produkt 1

HCID 534237412-Acetamidocinnamic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

In the process for the preparation of N-acetylphenylalanine by opening the ring of 2-methyl-4-benzylidene-1,3-oxazolin-5-one with water to give 2-acetaminocinnamic acid and subsequently catalytically hydrogenating the latter, both reaction stages are carried out in a mixture of an aliphatic C3 -ketone to C10 -ketone or a water-miscible ether and water as the solvent, and the hydrogenation of the 2-acetaminocinnamic acid is carried out at temperatures of 10° to 50° C. and pressures of 1 to 15 bar in the presence of a supported palladium catalyst.

Quellen und Nachweise

ORD-Eintrag
ord-fd8235dd3e864652bf90a61e2daa516b
Quelldatensatz
uspto-grants-1990_01
Patentnummer
US04892971

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