Trifluoroacetic acid → L-Phenylalanyl-L-alanine

HRID 223103

Reaktionsgleichung

Reaktionsgleichung von HRID 223103
C([O:5][C:6]([C@@H:8]([N:10]1[C@H:13]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C@H:12]([N:20]=[N+]=[N-])[C:11]1=[O:23])[CH3:9])=[O:7])(C)(C)C.[F:24][C:25]([F:30])([F:29])[C:26]([OH:28])=[O:27]>[Pd]>[F:24][C:25]([F:30])([F:29])[C:26]([OH:28])=[O:27].[NH2:20][C@H:12]([C:11]([NH:10][C@H:8]([C:6]([OH:7])=[O:5])[CH3:9])=[O:23])[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Komponenten

5

Edukt 2

HCID 6422Trifluoroacetic acidHCID 130352141-(1(S)-t-butoxycarbonylethyl)-3(S)-azido-4(R)-phenylazetidin-2-one

Produkt 2

HCID 6422Trifluoroacetic acidHCID 5488196L-Phenylalanyl-L-alanineAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 23938PalladiumKatalysator

Versuchsvorschrift

After 1-(1(S)-t-butoxycarbonylethyl)-3(S)-azido-4(R)-phenylazetidin-2-one (300 mg., 0.95 mmol) was stirred in trifluoroacetic acid (2 ml.) at room temperature for 15 hours, the solvent was removed by distillation under reduced pressure. The thus obtained oil (360 mg.) was hydrogenated in 25 ml. of ethanol at 50° C. for 15 hours under ambient pressure using a 10% Pd-C (300 mg.) as a catalyst to give trifluoroacetic acid salt of L-phenylalanyl-L-alanine (311 mg., yield: 94%).

Aufarbeitung

  1. customthe solvent was removed by distillation under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-8446506b615d4f04850806817179a906
Quelldatensatz
uspto-grants-1982_10
Patentnummer
US04352752

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