Reaktion #49195

Reaktionsgleichung

Compound 66

(6-{3-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-pyrrolidin-1-yl}-6-oxo-hexyl)-carbamic acid 17-(1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester

succinic anhydride

triethylamine

→

compound 68

Ausbeute 91.2%

Succinic acid mono-(4-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-1-{6-[17-(1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yloxycarbonylamino]-hexanoyl}-pyrrolidin-3-yl)ester

Ausbeute 91.2%

Lösungsmittel

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigedried in a vacuum at 40° C. overnight
2. 2
   workup.DISSOLUTIONThe mixture was dissolved in anhydrous dichloromethane (50 mL)
3. 3
   Waschenwashed with ice cold aqueous citric acid (5% wt., 100 mL) and water (2×100 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 17, Compound 66(12 g, 12.69 mmol) was mixed with succinic anhydride (1.9 g, 19 mmol) and DMAP (1.56 g, 13 mmol) and dried in a vacuum at 40° C. overnight. The mixture was dissolved in anhydrous dichloromethane (50 mL), triethylamine (2 g, 3.6 mL, 26 mmol) was added and the solution was stirred at room temperature under argon atmosphere for 16 h. It was then diluted with dichloromethane (100 mL) and washed with ice cold aqueous citric acid (5% wt., 100 mL) and water (2×100 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 68 as white solid (12.1 g, 91% yield; Rf=0.5 in 10% MeOH/CHCl3).

Quelle