반응 #76252

반응 방정식

ammonium chloride

5-(2-phtalimidoethyl)-1-(β-D-ribopyranosyl)uracil

benzoyl chloride

→

1-(2′-O-benzoyl-β-D-ribopyranosyl)-5-(2-phtalimidoethyl)uracil

용매

pyridine

pyridine

dichloromethane

반응 조건

후처리

1. 1
   온도a heated
2. 2
   기타argon-flushed 1 l four-necked flask
3. 3
   workup.ADDITIONmixed with 200 ml of dichloromethane
4. 4
   온도with cooling
5. 5
   추출the aqueous phase was extracted with ethyl acetate
6. 6
   세척The combined organic phases were washed with water
7. 7
   기타dried
8. 8
   농축concentrated to dryness in vacuo

실험 절차

10.6 g (0.025 mmol) of 5-(2-phtalimidoethyl)-1-(β-D-ribopyranosyl)uracil were dissolved in 20 ml of pyridine in a heated and argon-flushed 1 l four-necked flask and mixed with 200 ml of dichloromethane. The mixture was cooled to −70° C., 3.82 ml (0.033 mmol) of benzoyl chloride in 5 ml of pyridine and 20 ml of dichloromethane were slowly added dropwise with cooling and the mixture was stirred at −70° C. for 35 min. The reaction mixture was poured onto 600 ml of cooled ammonium chloride solution and the aqueous phase was extracted with ethyl acetate. The combined organic phases were washed with water, dried and concentrated to dryness in vacuo. Chromatography on silica gel (ethyl acetate/heptane 1:1) yielded 7.9 g (60%) of 1-(2′-O-benzoyl-β-D-ribopyranosyl)-5-(2-phtalimidoethyl)uracil.

출처