تفاعل #49204

معادلة التفاعل

Lithocholic acid

Isobutylchloroformate

triethylamine

dioctadecylamine

→

amide

المردود 93.8%

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

المردود 93.8%

المذيبات

tetrahydrofuran

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

Lithocholic acid (81) (7.1 g, 18.8 mmol) was sissolved in anhydrous tetrahydrofuran (60 mL). Isobutylchloroformate (2.6 g, 2.6 mL, 18.8 mmol) was added followed by the addition of triethylamine (3.84 g, 5.3 mL, 38 mmol) and dioctadecylamine (9.8 g, 18.77 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 82 (15.5 g) in 93% yield. This was used as such for the next step.

المصدر