Sodium Hydroxide → 2-(4-Amino-3-carboxymethylphenyl)propionic acid disodium salt

HRID 1873232Notes

Reaction equation

HRID 1873232 reaction equation
[C:1]([CH2:4][C:5]1[CH:6]=[C:7]([CH:14]([CH3:18])[C:15]([OH:17])=[O:16])[CH:8]=[CH:9][C:10]=1[N+:11]([O-])=O)([OH:3])=[O:2].[H][H].[OH-].[Na+:22]>[Pd]>[Na+:22].[Na+:22].[NH2:11][C:10]1[CH:9]=[CH:8][C:7]([CH:14]([CH3:18])[C:15]([O-:17])=[O:16])=[CH:6][C:5]=1[CH2:4][C:1]([OH:3])=[O:2].[NH2:11][C:10]1[CH:9]=[CH:8][C:7]([CH:14]([CH3:18])[C:15]([O-:17])=[O:16])=[CH:6][C:5]=1[CH2:4][C:1]([OH:3])=[O:2]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 186886652-(3-Carboxymethyl-4-nitrophenyl)propionic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 1317219662-(4-Amino-3-carboxymethylphenyl)propionic acid disodium saltYield 91.7%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

In 1N aqueous sodium hydroxide solution (6 mL) was dissolved 2-(3-carboxymethyl-4-nitrophenyl)propionic acid (obtained in Example 1, 760 mg, 3 mmol.). The solution was stirred for 18 hours at room temperature in a hydrogen gas atmosphere, after addition of 1006 palladium/carbon (15 mg). Insolubles were removed by filtration, and the filtrate was concentrated under reduced pressure to give a brown crystalline product. The obtained crystalline product was washed successively with ethanol and hexane to give 734 mg (yield: 91.7%) of the desired compound as a white crystalline product.

Workup

  1. customInsolubles were removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customto give a brown crystalline product
  4. washThe obtained crystalline product was washed successively with ethanol and hexane

Sources & evidence

ORD record
ord-8057fdb537f0406192a757ea273afb19
Source dataset
uspto-grants-2000_08
Patent number
US06111115

Reaction notes

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