Reaktion #49174

Reaktionsgleichung

Compound 12

(6-[2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-pyrrolidin-1-yl]-6-oxo-hexyl)-carbamic acid 2,3-bis-octadecyloxy-propyl ester

succinic anhydride

triethylamine

→

compound 14

Ausbeute 47.3%

Succinic acid mono-{5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-1-[6-(2,3-bis-octadecyloxy-propoxycarbonylamino)-hexanoyl]-pyrrolidin-3-yl}ester

Ausbeute 47.3%

Lösungsmittel

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigedried in a vacuum at 40° C. overnight
2. 2
   workup.DISSOLUTIONThe mixture was dissolved in anhydrous dichloromethane (20 mL)
3. 3
   Waschenwashed with ice cold aqueous citric acid (5% wt., 50 mL) and water (2×50 mL)
4. 4
   TrocknenThe organic phase was dried over anhydrous sodium sulfate
5. 5
   Einengenconcentrated to dryness
6. 6
   SonstigeThe crude product was purified by column chromatography

Vorschrift

Referring to scheme 5, Compound 12 (5.6 g, 4.8 mmol) was mixed with succinic anhydride (0.727 g, 7.26 mmol) and DMAP (0.062 g, 0.5 mmol) and dried in a vacuum at 40° C. overnight. The mixture was dissolved in anhydrous dichloromethane (20 mL), triethylamine (1.52 g, 2 mL, 15 mmol) was added and the solution was stirred at room temperature under argon atmosphere for 16 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 to afford compound 14 as white solid (2.85 g, 47% yield; Rf=0.65 in 10% MeOH/CHCl3).

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