Reacción #49205

Ecuación de reacción

amide

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

disuccinimidyl carbonate

triethylamine

acetonitrile

→

Compound 83

Rendimiento 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

Rendimiento 71.0%

Disolventes

dichloromethane

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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.

Fuente