Beta-Alanine → 3-Phthalimidopropionic acid

HRID 520304Notes

Reaction equation

HRID 520304 reaction equation
[C:1]1(=[O:11])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](=[O:10])O1.[NH2:12][CH2:13][CH2:14][C:15]([OH:17])=[O:16]>O>[O:10]=[C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[C:1](=[O:11])[N:12]1[CH2:13][CH2:14][C:15]([OH:17])=[O:16]

Participants

4

Reactant 2

HCID 239Beta-AlanineHCID 6811Phthalic Anhydride

Product 1

HCID 768593-Phthalimidopropionic acidYield 69%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
170 °C

Procedure

A mixture of isobenzofuran-1,3-dione (20 g, 135 mmol) and 3-aminopropanoic acid (12 g, 135 mmol) was stirred at 170° C. for 6 h. See FIG. 2. Upon reaction completion, the mixture was diluted with water and extracted with DCM (100 mL×3). The combined organic layers were dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to give 3-(1,3-dioxoisoindolin-2-yl)propanoic acid 137g (20 g, 69%) as a white solid.

Workup

  1. customUpon reaction completion
  2. extractionextracted with DCM (100 mL×3)
  3. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f7747a0545614a7db3269e1fdf0c0420
Source dataset
uspto-grants-2016_05
Patent number
US09326985B2

Reaction notes

Loading…