Pyruvic Acid → HCID 70377804, compound

HRID 620231Notes

Reaction equation

HRID 620231 reaction equation
C([NH:11][C@H:12]([C:14]([N:16]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH2:17][C:18]([OH:20])=[O:19])=[O:15])[CH3:13])(OCC1C=CC=CC=1)=O.[C:28]([OH:33])(=[O:32])[C:29]([CH3:31])=[O:30]>C(O)C.[Pd]>[C:28]([OH:33])(=[O:32])[C:29]([CH3:31])=[O:30].[C:28]([CH:29]([NH:11][C@H:12]([C:14]([N:16]([CH2:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[CH2:17][C:18]([OH:20])=[O:19])=[O:15])[CH3:13])[CH3:31])([OH:33])=[O:32]

Participants

5

Reactant 2

HCID 1060Pyruvic AcidHCID 15615016HCID 15615016, compound

Product 1

HCID 70377804HCID 70377804, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of N-carbobenzyloxy-L-alanyl-N-benzyl glycine (5.8 g, 15.6 mmol) and pyruvic acid (3.5 g, 39.1 mmol) in 200 ml absolute ethanol was added 10% palladium on carbon (0.5 g). The mixture was hydrogenated at 50 psi for 4 hours. The solution was filtered and concentrated in vacuo at room temperature. The residue was dissolved in H2O and ethyl acetate. The aqueous layer was washed twice with ethyl acetate and once with ether and lyophilized to provide the crystalline product, m.p. 105°-108° C.

Workup

  1. filtrationThe solution was filtered
  2. concentrationconcentrated in vacuo at room temperature
  3. dissolutionThe residue was dissolved in H2O
  4. washThe aqueous layer was washed twice with ethyl acetate and once with ether
  5. customto provide the crystalline product, m.p. 105°-108° C.

Sources & evidence

ORD record
ord-57b6a7c45151463f94a564b2d6ef8c2f
Source dataset
uspto-grants-1989_04
Patent number
US04820729

Reaction notes

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