Réaction #3770

Équation de réaction

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

Solvants

dichloromethane

Conditions de réaction

Traitement

1. 1
   TempératureHeat
2. 2
   TempératureContinue heating
3. 3
   Températureat reflux
4. 4
   AutrePass the refluxate through oven dried 4 Å molecular sieves
5. 5
   ExtractionExtract with 5% sodium bicarbonate solution
6. 6
   ExtractionExtract the 5% sodium bicarbonate solution with dichloromethane
7. 7
   Autredry over Na2 SO4
8. 8
   Filtrationfilter
9. 9
   Autreevaporate in vacuo
10. 10
    Autreto give a residue

Mode opératoire

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.

Source