Реакция #10554

Уравнение реакции

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

Выход 78.0%

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

Выход 78.0%

Растворители

THF

Условия реакции

Обработка

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

Методика

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%).

Источник