Réaction #49203

Équation de réaction

Compound 77

2-(6-{3-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-pyrrolidin-1-yl}-6-oxo-hexyl)-isoindole-1,3-dione

succinic anhydride

triethylamine

→

compound 79

Rendement 89.6%

Succinic acid mono-{4-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-1-[6-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-hexanoyl]-pyrrolidin-3-yl}ester

Rendement 89.6%

Solvants

dichloromethane

Conditions de réaction

Traitement

1. 1
   Autredried in a vacuum at 40° C. overnight
2. 2
   workup.DISSOLUTIONThe mixture was dissolved in anhydrous dichloromethane (5 mL)
3. 3
   Lavagewashed with ice cold aqueous citric acid (5% wt., 50 mL) and water (2×50 mL)
4. 4
   SéchageThe organic phase was dried over anhydrous sodium sulfate
5. 5
   Concentrationconcentrated to dryness
6. 6
   AutreThe crude product was purified by column chromatography

Mode opératoire

Referring to scheme 19, Compound 77 (2 g, 3 mmol) was mixed with succinic anhydride (0.600 g, 6 mmol) and DMAP (0.366 g, 3 mmol) and dried in a vacuum at 40° C. overnight. The mixture was dissolved in anhydrous dichloromethane (5 mL), triethylamine (0.913 g, 1.25 mL, 9 mmol) was added and the solution was stirred at room temperature under argon atmosphere for 4 h. It was then diluted with dichloromethane (50 mL) and washed with ice cold aqueous citric acid (5% wt., 50 mL) and water (2×50 mL). The organic phase was dried over anhydrous sodium sulfate and concentrated to dryness. The crude product was purified by column chromatography using 6% MeOH/DCM to afford compound 79 as white solid (2.05 g, 89% yield; Rf=0.4 in 10% MeOH/CHCl3).

Source