Reacción #3770

Ecuación de reacción

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

Disolventes

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaHeat
2. 2
   TemperaturaContinue heating
3. 3
   Temperaturaat reflux
4. 4
   OtroPass the refluxate through oven dried 4 Å molecular sieves
5. 5
   ExtracciónExtract with 5% sodium bicarbonate solution
6. 6
   ExtracciónExtract the 5% sodium bicarbonate solution with dichloromethane
7. 7
   Otrodry over Na2 SO4
8. 8
   Filtraciónfilter
9. 9
   Otroevaporate in vacuo
10. 10
    Otroto give a residue

Procedimiento

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.

Fuente