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

HRID 466733노트

반응식

HRID 466733 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 1049Pyridine용매

반응 조건

온도
50 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-bcbd2a519bfb4ddc87d97494e1eac672
출처 데이터셋
uspto-grants-1992_10
특허 번호
US05157114

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