Ethanol → N-Acetyl-L-phenylalanine

HRID 596177

Reaktionsgleichung

Reaktionsgleichung von HRID 596177
PP.C(O)C.[C:6]([NH:9][C:10](=[CH:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:11]([OH:13])=[O:12])(=[O:8])[CH3:7].[H][H]>C(N(CC)CC)C>[C:6]([NH:9][C@H:10]([C:11]([OH:13])=[O:12])[CH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)(=[O:8])[CH3:7]

Komponenten

6

Edukt 4

HCID 702EthanolHCID 956312-(Acetylamino)-3-phenyl-2-propenoic acidHCID 139283DiphosphaneHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 74839N-Acetyl-L-phenylalanineAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

3.1 mg of the complex of the formula [RhCl-1,5-cyclooctadiene]2, 57 mg of the diphosphine of Example 1 and 400 cm3 of ethyl alcohol are introduced under an argon atmosphere into a reactor. The mixture is stirred for 1 hour. 66.62 g of α-acetamidocinnamic acid and 25 microlitres of triethylamine are then added and hydrogen is introduced under a pressure of 1 bar at 25° C. After 4 hours 30 minutes the hydrogenation is complete. After treatment to remove the catalyst similar to that of Example 5, N-acetylphenylalanine is obtained, after extraction, in 97% chemical yield and with an optical rotation [α]D22 of 42.5° (optical yield 82%).

Aufarbeitung

  1. waitAfter 4 hours 30 minutes the hydrogenation is complete
  2. customAfter treatment to remove the catalyst similar to that of Example 5

Quellen und Nachweise

ORD-Eintrag
ord-7b78a90c575e417c880f20ee6c4b724e
Quelldatensatz
uspto-grants-1977_03
Patentnummer
US04010181

Verknüpfte Notizen

Wird geladen…