Ethyl pyruvate → N-(Phenyl-furazan-3-yl)-D,L-alanine

HRID 23011

Reaktionsgleichung

Reaktionsgleichung von HRID 23011
[C:1]1([C:7]2[C:8]([NH2:12])=[N:9][O:10][N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:13]([O:18]CC)(=[O:17])[C:14]([CH3:16])=O>C(O)C.[Pt]>[C:1]1([C:7]2[C:8]([NH:12][CH:14]([C:13]([OH:18])=[O:17])[CH3:16])=[N:9][O:10][N:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Komponenten

5

Edukt 2

HCID 12041Ethyl pyruvateHCID 1391324-Phenyl-1,2,5-oxadiazol-3-amine

Produkt 1

HCID 22312046N-(Phenyl-furazan-3-yl)-D,L-alanine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23939PlatinumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

4-Phenyl-furazan-3-ylamine (Maybridge) and ethyl pyruvate (Aldrich) were dissolved in dry ethanol. Platinum on sulfide carbon (5%) was added and the resulting mixture was hydrogenated (1000 psi, H2) at 150° C. for 8 hours. The reaction mixture was then filtered through Celite and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel chromatography using CHCl3 as the eluent to provide the title compound as its ethyl ester. The ethyl ester was then hydrolyzed using General Procedure II-A, Method B (LiOH/H2O/dioxane) to provide the title compound.

Aufarbeitung

  1. customat 150° C.
  2. customfor 8 hours
  3. filtrationThe reaction mixture was then filtered through Celite
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-7c1ca55354a64663aaf7a45118fb74d9
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06849650B2

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