تفاعل #3770

معادلة التفاعل

p-toluenesulfonic acid

tetrahydrofuran dichloromethane

phthalimido-(S)-phenyalanine amide

glutaric dialdehyde

water

→

title compound

(S)-N-[2-(1,3-Dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-oxo-3-phenylpropyl]-1,4-dihydro-pyridine

المذيبات

dichloromethane

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةHeat
2. 2
   درجة الحرارةContinue heating
3. 3
   درجة الحرارةat reflux
4. 4
   أخرىPass the refluxate through oven dried 4 Å molecular sieves
5. 5
   استخلاصExtract with 5% sodium bicarbonate solution
6. 6
   استخلاصExtract the 5% sodium bicarbonate solution with dichloromethane
7. 7
   أخرىdry over Na2 SO4
8. 8
   ترشيحfilter
9. 9
   أخرىevaporate in vacuo
10. 10
    أخرىto give a residue

الإجراء التجريبي

Combine phthalimido-(S)-phenyalanine amide (3.0 g, 10 mmol) and a solution of glutaric dialdehyde (2.0 g; 50% by weight in water) in dichloromethane (200 mL). Heat to reflux with azeotropic removal of water from the refluxate. Add p-toluenesulfonic acid (60 mg). Continue heating at reflux. Pass the refluxate through oven dried 4 Å molecular sieves. After 4 days, cool the reaction mixture to ambient temperature. Extract with 5% sodium bicarbonate solution. Extract the 5% sodium bicarbonate solution with dichloromethane. Combine the organic layers and dry over Na2 SO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting with 5% tetrahydrofuran/dichloromethane to give the title compound.

المصدر