反应 #49207

反应方程式

Lithocholic acid

Isobutylchloroformate

triethylamine

dioctadecylamine

→

amide

收率 172.2%

4-(3-Hydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-pentanoic acid octadecylamide

收率 172.2%

溶剂

tetrahydrofuran

反应条件

后处理

1. 1
   其他was brought to ambient temperature
2. 2
   浓缩The reaction mixture was concentrated under vacuum
3. 3
   workup.DISSOLUTIONthe residue was dissolved in dichloromethane (250 mL)
4. 4
   洗涤The organic layer was washed with 5% sodium bicarbonate, 3% aqueous HCl and water
5. 5
   干燥After drying over anhydrous sodium sulfate
6. 6
   其他the solvent was removed under reduced pressure

实验过程

Lithocholic acid (81) (9.78 g, 26 mmol) was sissolved in anhydrous tetrahydrofuran (60 mL). Isobutylchloroformate (3.55 g, 3.55 mL, 26 mmol) was added followed by the addition of triethylamine (5.26 g, 7.25 mL, 52 mmol) and dioctadecylamine (7 g, 26 g). The reaction mixture was brought to ambient temperature and allowed to stir over night. The reaction mixture was concentrated under vacuum, and the residue was dissolved in dichloromethane (250 mL). The organic layer was washed with 5% sodium bicarbonate, 3% aqueous HCl and water. After drying over anhydrous sodium sulfate, the solvent was removed under reduced pressure to afford amide 88 (14.5 g) in 89% yield. This was used as such for the next step.

来源