Beta-Alanine → 3-Phthalimidopropionic acid

HRID 2211246Notes

Reaction equation

HRID 2211246 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]([OH:6])=[O:5].C(=O)([O-])[O-].[Na+].[Na+].C(N1[C:22](=[O:23])[C:21]2=[CH:24][CH:25]=[CH:26][CH:27]=[C:20]2[C:19]1=[O:28])(OCC)=O>O>[CH:25]1[CH:24]=[C:21]2[C:22]([N:1]([CH2:2][CH2:3][C:4]([OH:6])=[O:5])[C:19](=[O:28])[C:20]2=[CH:27][CH:26]=1)=[O:23]

Participants

5

Reactant 3

HCID 239Beta-AlanineHCID 10340Sodium CarbonateHCID 31187N-Carbethoxyphthalimide

Product 1

HCID 768593-Phthalimidopropionic acidYield 64%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred mixture of β-alanine (4.45 g, 50.0 mmol) and sodium carbonate (5.35 g, 50.5 mmol) in 100 mL of water is added N-carbethoxyphthalimide (10.95 g, 50.0 mmol). After 1.5 hour, the reaction slurry is filtered. The filtrate is stirred and the pH adjusted to 1-2 with 4N hydrochloric acid. After 15 minutes, the resulting slurry is filtered and the solid washed with water. The solid is dried in vacuo (60° C., <1 mm) to afford 6.96 g (64%) of N-phthaloyl-β-alanine, which can be alternatively named as 3-phthalimido-3-phenylpropionic acid, as a white powder.

Workup

  1. filtrationthe reaction slurry is filtered
  2. waitAfter 15 minutes
  3. filtrationthe resulting slurry is filtered
  4. washthe solid washed with water
  5. customThe solid is dried in vacuo (60° C., <1 mm)

Sources & evidence

ORD record
ord-8185fba57dae42c4a82f58ee6aaa8bde
Source dataset
uspto-grants-1995_10
Patent number
US05463063

Reaction notes

Loading…