反応 #10554

反応方程式

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

収率 78.0%

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

収率 78.0%

溶媒

THF

反応条件

後処理

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

実験手順

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%).

出典