4-Methylbenzoyl Chloride → 2',3'-Dideoxy-3'-fluoro-5'-O-p-toluoyluridine

HRID 466733ノート

反応式

HRID 466733 の反応式
[F:1][C@@H:2]1[C@@H:6]([CH2:7][OH:8])[O:5][C@@H:4]([N:9]2[CH:16]=[CH:15][C:13](=[O:14])[NH:12][C:10]2=[O:11])[CH2:3]1.[C:17]1([CH3:26])[CH:22]=[CH:21][C:20]([C:23](Cl)=[O:24])=[CH:19][CH:18]=1>N1C=CC=CC=1>[F:1][C@@H:2]1[C@@H:6]([CH2:7][O:8][C:23]([C:20]2[CH:21]=[CH:22][C:17]([CH3:26])=[CH:18][CH:19]=2)=[O:24])[O:5][C@@H:4]([N:9]2[CH:16]=[CH:15][C:13](=[O:14])[NH:12][C:10]2=[O:11])[CH2:3]1

参加物

4

反応物 2

HCID 134054-Methylbenzoyl ChlorideHCID 1624502',3'-Dideoxy-3'-fluorouridine

生成物 1

HCID 186483722',3'-Dideoxy-3'-fluoro-5'-O-p-toluoyluridine

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

反応条件

温度
50 °C

実験手順

To a stirred solution of 2',3'-dideoxy-3'-fluorouridine (1 g, 4.34 mmoles) in dry pyridine (25 ml) at 0° C. was slowly added freshly distilled p-toluoyl chloride (0.63 ml, 4.78 mmoles). After the addition was complete, the mixture was stirred at 50° C. for 1.5 hrs., cooled and the solvent removed under reduced pressure. The residue was dissolved in chloroform (35 ml) and the solution extracted with 1M sulphuric acid (2×20 ml), water (2×30 ml) and dried (sodium sulphate). Evaporation of the solvent and purification of the residue by silica column chromatography eluting with 5% MeOH/CH2Cl2 afforded the title compound.

後処理

  1. additionAfter the addition
  2. temperature, cooled
  3. customthe solvent removed under reduced pressure
  4. dissolutionThe residue was dissolved in chloroform (35 ml)
  5. extractionthe solution extracted with 1M sulphuric acid (2×20 ml), water (2×30 ml)
  6. dry with materialdried (sodium sulphate)
  7. customEvaporation of the solvent and purification of the residue by silica column chromatography
  8. washeluting with 5% MeOH/CH2Cl2

出典と根拠

ORDレコード
ord-bcbd2a519bfb4ddc87d97494e1eac672
出典データセット
uspto-grants-1992_10
特許番号
US05157114

反応ノート

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