Beta-Alanine → 3-Phthalimidopropionic acid

HRID 1421284Notes

Reaction equation

HRID 1421284 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 4 N 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-c1316fa6c4984840a655b7457ac42d10
Source dataset
uspto-grants-2000_06
Patent number
US06075041

Reaction notes

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