Floxuridine → 3-Benzoyl-2'-deoxy-5-fluorouridine

HRID 477168

반응식

HRID 477168 반응식
[F:1][C:2]1[C:3](=[O:17])[NH:4][C:5](=[O:16])[N:6]([CH:15]=1)[C@@H:7]1[O:14][C@H:11]([CH2:12][OH:13])[C@@H:9]([OH:10])[CH2:8]1.C(N(CC)CC)C.[C:25](Cl)(=[O:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>CC(N(C)C)=O>[C:25]([N:4]1[C:3](=[O:17])[C:2]([F:1])=[CH:15][N:6]([C@@H:7]2[O:14][C@H:11]([CH2:12][OH:13])[C@@H:9]([OH:10])[CH2:8]2)[C:5]1=[O:16])(=[O:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

참가 물질

5

반응물 3

HCID 5790FloxuridineHCID 7412Benzoyl chlorideHCID 8471Triethylamine

생성물 1

HCID 133057643-Benzoyl-2'-deoxy-5-fluorouridine

시약·촉매·용매 1

HCID 31374Dimethylacetamide용매

실험 절차

15 Grams of 2'-deoxy-5-fluoro uridine (FudR) was dissolved in 45 ml of dimethylacetamide. Thereto was added 9 ml of triethylamine. To the mixture being cooled with ice-water was added 8.6 g of benzoyl chloride and the whole mixture was stirred overnight. The reaction mixture was subjected to filtration. The resulting filtrate was subjected to evaporation to obtain the residue, and water was added to the residue. The aqueous solution was extracted with ethyl acetate, and the organic layer was dried with anhydrous sodium sulfate. The dried ethyl acetate solution was concentrated and the residue was recrystallized from ethanol to obtain the desired compound. The yield was 10.5 g. M.p. 126° to 127° C.

후처리

  1. filtrationThe reaction mixture was subjected to filtration
  2. customThe resulting filtrate was subjected to evaporation
  3. customto obtain the residue, and water
  4. additionwas added to the residue
  5. extractionThe aqueous solution was extracted with ethyl acetate
  6. dry with materialthe organic layer was dried with anhydrous sodium sulfate
  7. concentrationThe dried ethyl acetate solution was concentrated
  8. customthe residue was recrystallized from ethanol

출처 및 근거

ORD 기록
ord-e8666096cdf1472fa2c75f3848ee82ba
출처 데이터셋
uspto-grants-1989_12
특허 번호
US04886877

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