تفاعل #322159

معادلة التفاعل

methanol

5'-O-(t-Butyldimethylsilyl)-2',3'-dideoxy-3'-(N,N-dimethylamino-methylene)-2'-oxo-uridine

trifluoromethanesulfonyl azide

→

title compound

المردود 77.0%

5'-O-(t-Butyldimethylsilyl)-2',3'-dideoxy-3'-diazo-2'-oxo-uridine

المردود 77.0%

المذيبات

methylene chloride

ظروف التفاعل

المعالجة

1. 1
   أخرىThe solvents were evaporated in vacuo to a syrup (2.8 g) which
2. 2
   workup.DISSOLUTIONwas dissolved in 10 mL of methylene chloride
3. 3
   أخرىpurified by flash chromatography (5 psi) on a silica gel column (2×35 cm)
4. 4
   غسيلeluted with 200 mL of methylene chloride, 200 mL of 1% methanol in methylene chloride, 200 mL of 2% methanol in methylene chloride

الإجراء التجريبي

5'-O-(t-Butyldimethylsilyl)-2',3'-dideoxy-3'-(N,N-dimethylamino-methylene)-2'-oxo-uridine (1.78 g, 4.5 mmol), from Step 6, was added to the trifluoromethanesulfonyl azide solution and the reaction mixture was heated at 60° C. for 2.5 h under a nitrogen atmosphere. The solvents were evaporated in vacuo to a syrup (2.8 g) which was dissolved in 10 mL of methylene chloride and purified by flash chromatography (5 psi) on a silica gel column (2×35 cm) eluted with 200 mL of methylene chloride, 200 mL of 1% methanol in methylene chloride, 200 mL of 2% methanol in methylene chloride and 3% methanol in methylene chloride to give 1.27 g (77% yield) of the title compound. MS DCI: 367 (M+H)+.

المصدر