Reaktion #49205

Reaktionsgleichung

amide

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

disuccinimidyl carbonate

triethylamine

acetonitrile

→

Compound 83

Ausbeute 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

Ausbeute 71.0%

Lösungsmittel

dichloromethane

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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.

Quelle