Beta-Alanine → 3-Phthalimidopropionic acid

HRID 1417362Notes

Reaction equation

HRID 1417362 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-phthalimidopropionic 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-7316646b87dd448ea6b7445c3f427670
Source dataset
uspto-grants-1999_03
Patent number
US05877200

Reaction notes

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