반응 #49202

반응 방정식

2-cyanoethyl-N,N,N′,N′-tetraisopropylphosphorodiamidite

Compound 77

2-(6-{3-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-pyrrolidin-1-yl}-6-oxo-hexyl)-isoindole-1,3-dione

toluene

ethyl acetate

→

compound 78

수율 85.0%

Pyrrolidine phthalimido phosphoramidite

수율 85.0%

용매

hexane

반응 조건

후처리

1. 1
   건조the mixture was dried over P2O5 in a vacuum oven for overnight at 40° C
2. 2
   workup.DISSOLUTIONThe reaction mixture was dissolved in acetonitrile/dichloroethane (10 mL)
3. 3
   농축The reaction mixture was concentrated undervacuum
4. 4
   workup.DISSOLUTIONthe residue was dissolved in ethyl acetate (100 mL)
5. 5
   세척The organic layer was washed with 5% NaHCO3 (100 mL) and brine (100 mL)
6. 6
   건조The organic layer was dried over anhydrous Na2SO4
7. 7
   여과filtered
8. 8
   농축concentrated under reduced pressure
9. 9
   기타The residue was purified over silica gel (50:49:1, EtOAc:Hexane:triethlyamine)

실험 절차

Compound 77 (1.5 g, 2.26 mmol) was coevaporated with anhydrous toluene (25 mL). To the residue N,N-tetraisopropylammonium tetrazolide (0.127 g, 1.13 mmol) was added and the mixture was dried over P2O5 in a vacuum oven for overnight at 40° C. The reaction mixture was dissolved in acetonitrile/dichloroethane (10 mL) and 2-cyanoethyl-N,N,N′,N′-tetraisopropylphosphorodiamidite (1.362 g, 1.49 mL, 4.52 mmol) was added. The reaction mixture was stirred at ambient temperature for overnight. The completion of the reaction was ascertained by TLC (Rf=0.4 in 1:1 ethyl acetate:hexane). The reaction mixture was concentrated undervacuum and the residue was dissolved in ethyl acetate (100 mL). The organic layer was washed with 5% NaHCO3 (100 mL) and brine (100 mL). The organic layer was dried over anhydrous Na2SO4 filtered and concentrated under reduced pressure. The residue was purified over silica gel (50:49:1, EtOAc:Hexane:triethlyamine) to afford compound 78 as white solid (1.66 g, 85%).

출처