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

HRID 1634390Notes

Reaction equation

HRID 1634390 reaction equation
[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

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 702EthanolSolvent

Procedure

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 eluant 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.

Workup

  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

Sources & evidence

ORD record
ord-d1783252934642fab14a64c83d46719f
Source dataset
uspto-grants-2003_01
Patent number
US06506782B1

Reaction notes

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