Reaktion #450404

Reaktionsgleichung

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

Lösungsmittel

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturHeat
2. 2
   TemperaturContinue heating
3. 3
   Temperaturat reflux
4. 4
   SonstigePass the refluxate through oven dried 4 Å molecular sieves
5. 5
   ExtraktionExtract with 5% sodium bicarbonate solution
6. 6
   ExtraktionExtract the 5% sodium bicarbonate solution with dichloromethane
7. 7
   Trocknendry over Na2SO4
8. 8
   Filtrationfilter
9. 9
   Sonstigeevaporate invacuo
10. 10
    Sonstigeto give a residue

Vorschrift

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 Na2SO4, filter, and evaporate invacuo to give a residue. Chromatograph the residue on silica gel eluting with 5% tetrahydrofuran/dichloromethane to give the title compound.

Quelle