反応 #49207

反応方程式

Lithocholic acid

Isobutylchloroformate

triethylamine

dioctadecylamine

→

amide

収率 172.2%

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

収率 172.2%

溶媒

tetrahydrofuran

反応条件

後処理

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

実験手順

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.

出典