Phenylpyruvic acid → HCID 54264201, compound

HRID 2372596Notes

Reaction equation

HRID 2372596 reaction equation
[NH2:1][C@H:2]([C:4]([N:6]([CH:11]1[CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:12]1)[CH2:7][C:8]([OH:10])=[O:9])=[O:5])[CH3:3].[C:20]1([CH2:26][C:27](=O)[C:28]([OH:30])=[O:29])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C([BH3-])#N.[Na+]>[OH-].[K+]>[C:28]([CH:27]([NH:1][C@H:2]([C:4]([N:6]([CH:11]1[CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:12]1)[CH2:7][C:8]([OH:10])=[O:9])=[O:5])[CH3:3])[CH2:26][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)([OH:30])=[O:29]

Participants

5

Reactant 3

HCID 997Phenylpyruvic acidHCID 5003444Sodium cyanoborohydrideHCID 13132286HCID 13132286, compound

Product 1

HCID 54264201HCID 54264201, compoundYield 19.2%

Reagents, catalysts & solvents 1

HCID 14797Potassium HydroxideSolvent

Procedure

L-Alanyl-N-(indan-2-yl)glycine (1.0 g) and 6.0 g of phenylpyruvic acid are dissolved in 50 ml of 70% aqueous potassium hydroxide. Sodium cyanoborohydride (1.0 g) is added to this solution. After allowing the mixture to stand at room temperature overnight, the solvent is distilled off under reduced pressure, the residue is dissolved in 2 ml of water, made absorbed on a Dowex 50 (H+) [trade name of ion-exchange resin] column and eluted with 2% pyridine. The solvent is distilled off under reduced pressure, the residue is purified by silica gel column chromatography using acetonitrile-methanol (4:1) as the developer to give 0.3 g of N-(1-carboxy-2-phenylethyl)-L-alanyl-N-(indan-2-yl)glycine as colorless powder.

Workup

  1. distillationthe solvent is distilled off under reduced pressure
  2. dissolutionthe residue is dissolved in 2 ml of water
  3. custommade absorbed on a Dowex 50 (H+) [trade name of ion-exchange resin] column
  4. washeluted with 2% pyridine
  5. distillationThe solvent is distilled off under reduced pressure
  6. customthe residue is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-3a2e06124886434a938c44d27b8db71c
Source dataset
uspto-grants-1992_03
Patent number
US05098892

Reaction notes

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