Dimethylformamide dimethyl acetal → 5'-O-(t-Butyldimethylsilyl)-2',3'-dideoxy-3'-(N,N-dimethylaminomethylene)-2'-oxo-uridine

HRID 234976ノート

反応式

HRID 234976 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])[CH2:11]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].CO[CH:26](OC)[N:27]([CH3:29])[CH3:28]>CN(C)C=O>[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=[CH:26][N:27]([CH3:29])[CH3:28])([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:2])[CH3:3]

参加物

4

反応物 2

HCID 78373Dimethylformamide dimethyl acetalHCID 150596405'-O-(t-Butyldimethylsilyl)-2',3'-dideoxy-2'-oxo-uridine

生成物 1

HCID 677174835'-O-(t-Butyldimethylsilyl)-2',3'-dideoxy-3'-(N,N-dimethylaminomethylene)-2'-oxo-uridine収率 70%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
50 °C

実験手順

5'-O-(t-Butyldimethylsilyl)-2',3'-dideoxy-2'-oxo-uridine (2.2 g, 6.45 mmol) was dissolved in 25 mL of dry dimethylformamide (DMF) and 0.85 g (7.1 mmol) of N,N-dimethylformamide dimethyl acetal was added. The reaction mixture was heated to 50° C. under a nitrogen atmosphere and stirred for 0.5 h. The solvent was removed in vacuo and the residue (3.2 g) was dissolved in methylene chloride and purified by flash chromatography (5 psi) on a silica gel column (2×25 cm) eluted with 200 mL of methylene chloride, 200 mL of 2% methanol in methylene chloride and 200 mL of 5% methanol in methylene chloride to give 1.78 g (70% yield) of the title compound MS DCI: 396 (M+H)+, 418 (M+Na)+

後処理

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue (3.2 g) was dissolved in methylene chloride
  3. custompurified by flash chromatography (5 psi) on a silica gel column (2×25 cm)
  4. washeluted with 200 mL of methylene chloride, 200 mL of 2% methanol in methylene chloride and 200 mL of 5% methanol in methylene chloride

出典と根拠

ORDレコード
ord-cbd6a5f1937042d793336d2de49f7ef8
出典データセット
uspto-grants-1997_01
特許番号
US05597824

反応ノート

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