반응 #10554

반응 방정식

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

수율 78.0%

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

수율 78.0%

용매

THF

반응 조건

후처리

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

실험 절차

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%).

출처