تفاعل #440820
ord-d88b11484aee483eae22dcd2dd2cad4e
معادلة التفاعل
المتفاعلات
الكواشف
ظروف التفاعل
المعالجة
- 1درجة الحرارةThe mixture was heated
- 2درجة الحرارةunder reflux for 6 hours
- 3أخرىthe solvent was removed under reduced pressure
- 4درجة الحرارةThe resulting solution was then heated at 90° C. under a nitrogen atmosphere for 90 minutes
- 5درجة الحرارةThe mixture was cooled to room temperature
- 6غسيلwashed with a saturated aqueous solution of sodium hydrogen carbonate (350 ml)
- 7أخرىThe organic layer was separated
- 8تجفيفdried over anhydrous magnesium sulfate
- 9ترشيحfiltered
- 10أخرىevaporated under reduced pressure
- 11أخرىThe residue was purified by column chromatography on silica gel eluting with dichloromethane:methanol (98:2 by volume)
الإجراء التجريبي
A suspension of 2-amino-6-chloropurine (4.60 g, 27.13 mmol) in 1,1,1-trichloroethane (230 ml) was treated with N,O-bis(trimethylsilyl)acetamide (20 ml, 81.4 mmol). The mixture was heated under reflux for 6 hours. The solution was allowed to cool to room temperature and the solvent was removed under reduced pressure. The residue was treated with a solution of (2S,3S,4R,5R)- and (2S,3S,4R,5S)-5-acetyloxy)-4-benzoyloxy)-2-[(ethylamino)carbonyl]tetrahydro-3-furanyl benzoate (Preparation 14) (14.39 g, 32.6 mmol) in anhydrous toluene (230 ml) and trimethylsilyl trifluoromethanesulfonate (20 ml, 108.5 mmol). The resulting solution was then heated at 90° C. under a nitrogen atmosphere for 90 minutes. The mixture was cooled to room temperature, diluted with ethyl acetate (250 ml) and washed with a saturated aqueous solution of sodium hydrogen carbonate (350 ml) then brine (350 ml). The organic layer was separated, dried over anhydrous magnesium sulfate, filtered and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel eluting with dichloromethane:methanol (98:2 by volume) to afford the title compound as a foam (8.1 g).