تفاعل #1351725

معادلة التفاعل

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

المردود 60.1%

المذيبات

water

ظروف التفاعل

المعالجة

1. 1
   غسيلwash with methylene chloride (200 mL)
2. 2
   استخلاصextract with ethyl acetate (3×200 mL)
3. 3
   تجفيفdry (Na2SO4)
4. 4
   أخرىevaporate the solvent in vacuo
5. 5
   أخرىpurify by silica gel chromatography (1:1:0.02 hexane/ethyl acetate/acetic acid)
6. 6
   أخرىfollowed by recrystallization (isopropanol)

الإجراء التجريبي

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).

المصدر