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

HRID 234977

反応式

HRID 234977 の反応式
[Si:1]([O:8][CH2:9][C@H:10]1[O:14][C@@H:13]([N:15]2[CH:22]=[CH:21][C:19](=[O:20])[NH:18][C:16]2=[O:17])[C:12](=[O:23])[C:11]1=CN(C)C)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].FC(F)(F)S([N:33]=[N+:34]=[N-])(=O)=O.CO>C(Cl)Cl>[Si:1]([O:8][CH2:9][C@H:10]1[O:14][C@@H:13]([N:15]2[CH:22]=[CH:21][C:19](=[O:20])[NH:18][C:16]2=[O:17])[C:12](=[O:23])[C:11]1=[N+:33]=[N-:34])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

参加物

5

反応物 3

HCID 887MethanolHCID 10986786Methanesulfonyl azide, trifluoro-HCID 677174835'-O-(t-Butyldimethylsilyl)-2',3'-dideoxy-3'-(N,N-dimethylaminomethylene)-2'-oxo-uridine

生成物 1

HCID 867486945'-O-(t-Butyldimethylsilyl)-2',3'-dideoxy-3'-diazo-2'-oxo-uridine収率 77%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
60 °C

実験手順

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)+.

後処理

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

出典と根拠

ORDレコード
ord-fe624a0cbf0d4b9abc15969289b3308b
出典データセット
uspto-grants-1997_01
特許番号
US05597824

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