Reaction #1351725

Reaction equation

2-amino-3-(2-vinyl-phenyl)-propionic acid

sodium carbonate

N-carbethoxyphthalimide

→

2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-(2-vinyl-phenyl)-propionic acid

Yield 60.1%

Solvents

water

Conditions

Workup

1. 1
   Washwash with methylene chloride (200 mL)
2. 2
   Extractionextract with ethyl acetate (3×200 mL)
3. 3
   Dryingdry (Na2SO4)
4. 4
   Otherevaporate the solvent in vacuo
5. 5
   Otherpurify by silica gel chromatography (1:1:0.02 hexane/ethyl acetate/acetic acid)
6. 6
   Otherfollowed by recrystallization (isopropanol)

Procedure

Dissolve 2-amino-3-(2-vinyl-phenyl)-propionic acid (3.40 g) in water (75 mL) and add sodium carbonate (1.97 g, 18.6 mmol) and N-carbethoxyphthalimide (2.81 g, 12.8 mmol). Stir for 2.5 hours, wash with methylene chloride (200 mL), acidify to pH 1 with cold concentrated hydrochloric acid and extract with ethyl acetate (3×200 mL), dry (Na2SO4), evaporate the solvent in vacuo and purify by silica gel chromatography (1:1:0.02 hexane/ethyl acetate/acetic acid) followed by recrystallization (isopropanol) to give 2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-(2-vinyl-phenyl)-propionic acid as a pale yellow solid (2.47 g).

Source