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

HRID 23011

Reaction equation

HRID 23011 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 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.

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-7c1ca55354a64663aaf7a45118fb74d9
Source dataset
uspto-grants-2005_02
Patent number
US06849650B2

Linked notes

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