反应 #10554

反应方程式

n-Butyl nitrite

(2R,3R,4S,5S)-2-(2-amino-6-chloro-9H-purin-9-yl)-4-(benzoyloxy)-5-[(ethylamino)carbonyl]-tetrahydro-3-furanyl benzoate

iodine

diiodomethane

→

title compound

收率 78.0%

4-(Benzoyloxy)-2-(6-chloro-2-iodo-9H-purin-9-yl)-5-[(ethylamino)carbonyl]-tetrahydro-3-furanyl benzoate

收率 78.0%

溶剂

THF

反应条件

后处理

1. 1
   温度the mixture was heated
2. 2
   温度under reflux for 2.5 hours
3. 3
   其他the solvent was removed under reduced pressure
4. 4
   其他The residue was partitioned between aqueous sodium metabisulfite solution (5% w/v, 100 ml) and dichloromethane (100 ml)
5. 5
   其他The organic layer was separated
6. 6
   过滤filtered through Arbocel (trade mark)
7. 7
   干燥dried over anhydrous magnesium sulfate and solvent
8. 8
   其他evaporated under reduced pressure
9. 9
   其他The residue was purified by column chromatography on silica gel eluting with dichloromethane:methanol (99:1, by volume)

实验过程

n-Butyl nitrite (4.65 ml, 39.7 mmol) was added to a suspension of (2R,3R,4S,5S)-2-(2-amino-6-chloro-9H-purin-9-yl)-4-(benzoyloxy)-5-[(ethylamino)carbonyl]-tetrahydro-3-furanyl benzoate (Preparation 46) (8.10 g, 14.7 mmol), iodine (3.73 g, 14.7 mmol), copper(1) iodide (6.16 g, 32.3 mmol) and diiodomethane (12.55 ml, 155.8 mmol) in THF (100 ml) and the mixture was heated under reflux for 2.5 hours. The solution was allowed to cool to room temperature and the solvent was removed under reduced pressure. The residue was partitioned between aqueous sodium metabisulfite solution (5% w/v, 100 ml) and dichloromethane (100 ml). The organic layer was separated, filtered through Arbocel (trade mark), dried over anhydrous magnesium sulfate and solvent evaporated under reduced pressure. The residue was purified by column chromatography on silica gel eluting with dichloromethane:methanol (99:1, by volume) to afford the title compound as a yellow foam (7.55 g, 78%).

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