반응 #319549

반응 방정식

(2-bromophenyl)acetyl chloride

thionyl chloride

2',5'-dideoxy-5-ethyl-5'-methylaminouridine

→

5'-[2-(2-bromophenyl)-N-methylacetamido]-2',5'-dideoxy-5-ethyluridine

용매

methylene chloride methanol

benzene

benzene

pyridine

반응 조건

후처리

1. 1
   workup.WAITstored at 4° C. overnight
2. 2
   기타The solvents were removed by evaporation
3. 3
   기타the residue was re-evaporated with toluene
4. 4
   기타to give a gum which
5. 5
   기타was subsequently triturated with diethyl ether
6. 6
   기타to yield a solid
7. 7
   기타chromatographed on a column of silica gel
8. 8
   세척for the elution
9. 9
   workup.ADDITIONThe fractions containing the product
10. 10
    기타evaporated
11. 11
    기타The residue was re-evaporated with ethanol
12. 12
    기타recrystallized from methanol

실험 절차

0.72 g of 2',5'-dideoxy-5-ethyl-5'-methylaminouridine in 25 ml of dry pyridine was stirred at 0° C. and treated with a solution of (2-bromophenyl)acetyl chloride (prepared from 0.65 g of the acid by treatment with thionyl chloride in benzene under reflux) in 7 ml of benzene. The mixture was stirred at 0° C. for 0.5 hour and then stored at 4° C. overnight. The solvents were removed by evaporation and the residue was re-evaporated with toluene to give a gum which was subsequently triturated with diethyl ether to yield a solid. This solid was taken up in 5 ml of methylene chloride/methanol (9:1) and chromatographed on a column of silica gel using methylene chloride/methanol (9:1) for the elution. The fractions containing the product were combined and evaporated. The residue was re-evaporated with ethanol and recrystallized from methanol to give 0.18 g of 5'-[2-(2-bromophenyl)-N-methylacetamido]-2',5'-dideoxy-5-ethyluridine of melting point 182° -185° C.

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