Реакция #49173

Уравнение реакции

Compound 6

(6-{2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-pyrrolidin-1-yl}-6-oxo-hexyl)-carbamic Acid 10,13-dimethyl-17-octyl-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 8

Выход 89.5%

Succinic acid mono-{5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-1-[6-(10,13-dimethyl-17-octyl-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

Выход 89.5%

Растворители

dichloromethane

Условия реакции

Обработка

1. 1
   Другоеdried in a vacuum at 40° C. overnight
2. 2
   workup.DISSOLUTIONThe mixture was dissolved in anhydrous dichloromethane (50 mL)
3. 3
   Промывкаwashed with ice cold aqueous citric acid (5% wt., 100 mL) and water (2×100 mL)
4. 4
   СушкаThe organic phase was dried over anhydrous sodium sulfate
5. 5
   Концентрированиеconcentrated to dryness
6. 6
   ДругоеThe crude product was purified by column chromatography

Методика

Referring to scheme 3, Compound 6 (22 g, 23.2 mmol) was mixed with succinic anhydride (3.48 g, 34.8 mmol) and DMAP (0.283 g, 2.32 mmol) and dried in a vacuum at 40° C. overnight. The mixture was dissolved in anhydrous dichloromethane (50 mL), triethylamine (7 g, 9.6 mL, 70 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 8 as white solid (21.7 g, 89% yield; Rf=0.5 in 10% MeOH/CHCl3).

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