Pyruvic Acid → HCID 15614983, compound

HRID 620228Notes

Reaction equation

HRID 620228 reaction equation
C([NH:11][C@H:12]([C:14]([N:16]([C:21]1[CH:22]=[C:23]2[C:27](=[CH:28][CH:29]=1)[CH2:26][CH2:25][CH2:24]2)[CH2:17][C:18]([OH:20])=[O:19])=[O:15])[CH3:13])(OCC1C=CC=CC=1)=O.[C:30]([OH:35])(=[O:34])[C:31]([CH3:33])=[O:32]>C(O)C.[Pd]>[C:30]([OH:35])(=[O:34])[C:31]([CH3:33])=[O:32].[C:30]([CH:31]([NH:11][C@H:12]([C:14]([N:16]([C:21]1[CH:22]=[C:23]2[C:27](=[CH:28][CH:29]=1)[CH2:26][CH2:25][CH2:24]2)[CH2:17][C:18]([OH:20])=[O:19])=[O:15])[CH3:13])[CH3:33])([OH:35])=[O:34]

Participants

5

Reactant 2

HCID 1060Pyruvic AcidHCID 15614980HCID 15614980, compound

Product 1

HCID 15614983HCID 15614983, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of N-carbobenzoxy-L-alanyl-N-(5-indanyl)glycine (3.8 g, 9.59 mmol) and pyruvic acid (4.2 g, 47.9 mmol) in 200 ml ethanol was added 10% palladium on carbon (9.5 g). The mixture was hydrogenated at 50 psi for 4 h, filtered and concentrated in vacuo. The residue was dissolved in H2O and ethyl acetate. The aqueous layer was washed twice with ethyl acetate, once with ether, and lyophilized to provide the crystalline (m.p. 140° C. dec.) product.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in H2O
  4. washThe aqueous layer was washed twice with ethyl acetate, once with ether

Sources & evidence

ORD record
ord-55cc6e64ef0c4addb52a37883b98553f
Source dataset
uspto-grants-1989_04
Patent number
US04820729

Reaction notes

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