反応 #4982

反応方程式

2', 3'-dideoxycytidine

Iodine

→

iodide

収率 83.0%

5-iodo-2', 3'-dideoxycytidine

収率 83.0%

溶媒

methanol

methanol

dichloromethane

反応条件

後処理

1. 1
   workup.ADDITIONthe free base form of AG3 X4A resin (20 mL, 38 meq, Bio-Rad) was added
2. 2
   その他hydrogen sulfide was bubbled into the reaction for 15 minutes
3. 3
   その他Complete precipitation of mercury(II)
4. 4
   ろ過The reaction was filtered
5. 5
   ろ過through filter aid
6. 6
   洗浄the filter aid was washed with 1:1 methanol-dichloromethane
7. 7
   その他The filtrate was evaporated onto silica gel (10 g)
8. 8
   洗浄Elution

実験手順

A solution of 2', 3'-dideoxycytidine (2.11 g, 10 mmol, Raylo) and mercuric acetate (3.35 g, 10.5 mmol, Fisher) in 50 mL of methanol was refluxed for 19 hours. The resulting white suspension was diluted with methanol (50 mL) and dichloromethane (100 mL). Iodine (3.05 g, 12 mmol) was added and the suspension was stirred at 25°. After 4 hours, the free base form of AG3 X4A resin (20 mL, 38 meq, Bio-Rad) was added and hydrogen sulfide was bubbled into the reaction for 15 minutes. Complete precipitation of mercury(II) was verified by TLC. The reaction was filtered through filter aid and the filter aid was washed with 1:1 methanol-dichloromethane. The filtrate was evaporated onto silica gel (10 g) and the loaded siliva gel was placed on top of a 150 g silica gel column. Elution was 5%, 10%, and 20% methanol in dichloromethane afforded 2.79 g (83%) of iodide 19 as a colorless crystalline solid. Two recrystallizations form boiling water afforded, after vacuum-drying at 50°, large, analytically-pure prisms (mp: d 178° ).

出典