Water → 2'-deoxy-3'-O-benzyl-5'-O-trityl-5-fluorouridine

HRID 466102

反応式

HRID 466102 の反応式
[C:1]([O:20][CH2:21][C@H:22]1[O:26][C@@H:25]([N:27]2[CH:34]=[C:33]([F:35])[C:31](=[O:32])[NH:30][C:28]2=[O:29])[CH2:24][C@@H:23]1[OH:36])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:37](Br)[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1.[OH-].[K+].O>O1CCOCC1>[CH2:37]([O:36][C@@H:23]1[C@@H:22]([CH2:21][O:20][C:1]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[O:26][C@@H:25]([N:27]2[CH:34]=[C:33]([F:35])[C:31](=[O:32])[NH:30][C:28]2=[O:29])[CH2:24]1)[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1

参加物

6

反応物 4

HCID 962WaterHCID 7498Benzyl BromideHCID 14797Potassium HydroxideHCID 108387042'-deoxy-5'-O-trityl-5-fluorouridine

生成物 1

HCID 106747232'-deoxy-3'-O-benzyl-5'-O-trityl-5-fluorouridine収率 75.7%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

In 50 ml of dioxane was dissolved 10 g of 2'-deoxy-5'-O-trityl-5-fluorouridine. To the solution were added 2.9 ml of benzyl bromide and 14.6 g of particles of potassium hydroxide. The mixture was stirred at room temperature for 1 hour. Thereto was added 40 ml of water. The mixture was adjusted to a pH of about 3 to about 4 and extracted with ethyl acetate. The ethyl acetate layer was washed with an aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. The sodium sulfate was separated by filtration and the solvent was distilled off, giving as an intermediate 16.0 g of 2'-deoxy-3'-O-benzyl-5'-O-trityl-5-fluorouridine.

後処理

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with an aqueous solution of sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe sodium sulfate was separated by filtration
  5. distillationthe solvent was distilled off

出典と根拠

ORDレコード
ord-02a229dccd194282ba4a849f04e59d47
出典データセット
uspto-grants-1992_10
特許番号
US05155113

関連ノート

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