Réaction #49205

Équation de réaction

amide

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

disuccinimidyl carbonate

triethylamine

acetonitrile

→

Compound 83

Rendement 71.0%

Carbonic acid 17-(3-dioctadecylcarbamoyl-1-methyl-propyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-yl ester 2,5-dioxo-pyrrolidin-1-yl ester

Rendement 71.0%

Solvants

dichloromethane

Conditions de réaction

Traitement

1. 1
   Autreevaporated dryness
2. 2
   workup.DISSOLUTIONThe residue was dissolved in dichloromethane (300 mL)
3. 3
   LavageIt was washed with saturated NaHCO3 aqueous solution (3×100 mL)
4. 4
   SéchageThe organic layer was dried over Na2SO4
5. 5
   Filtrationfiltered
6. 6
   Autreevaporated to dryness

Mode opératoire

Referring to scheme 20, amide 82 (15.5 g, 17.6 mmol) was dissolved in anhydrous dichloromethane (150 mL). To the solution were added disuccinimidyl carbonate (6.76 g, 26.4 mmol), triethylamine (10 mL) and acetonitrile (50 mL). The reaction mixture was stirred at room temperature under argon for 6 h and then evaporated dryness. The residue was dissolved in dichloromethane (300 mL). It was washed with saturated NaHCO3 aqueous solution (3×100 mL). The organic layer was dried over Na2SO4, filtered and evaporated to dryness. Compound 83 (12.3 g, 71%) was obtained as colorless powder after drying in high vacuum, which was directly used for the next step without further purification.

Source