Phenylpyruvic acid → HCID 54264201, compound

HRID 621181Notes

Reaction equation

HRID 621181 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.[OH-].[K+].C([BH3-])#N.[Na+]>CO>[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

6

Reactant 4

HCID 997Phenylpyruvic acidHCID 14797Potassium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 13132286HCID 13132286, compound

Product 1

HCID 54264201HCID 54264201, compoundYield 19.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

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 methanol, and the pH is adjusted to 7.0 with 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 adsorbed 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. washeluted with 2% pyridine
  4. distillationThe solvent is distilled off under reduced pressure
  5. customthe residue is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-ee6dcac167584bf0b98b81f2858572b1
Source dataset
uspto-grants-1989_04
Patent number
US04822818

Reaction notes

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