Reacción #49207

Ecuación de reacción

Lithocholic acid

Isobutylchloroformate

triethylamine

dioctadecylamine

→

amide

Rendimiento 172.2%

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

Rendimiento 172.2%

Disolventes

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrowas brought to ambient temperature
2. 2
   ConcentraciónThe reaction mixture was concentrated under vacuum
3. 3
   workup.DISSOLUTIONthe residue was dissolved in dichloromethane (250 mL)
4. 4
   LavadoThe organic layer was washed with 5% sodium bicarbonate, 3% aqueous HCl and water
5. 5
   SecadoAfter drying over anhydrous sodium sulfate
6. 6
   Otrothe solvent was removed under reduced pressure

Procedimiento

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.

Fuente