Sodium → Doxifluridine

HRID 1759378

반응식

HRID 1759378 반응식
C([O:4][C@@H:5]1[C@H:9]([O:10]C(=O)C)[C@@H:8]([CH3:14])[O:7][C@H:6]1[N:15]1[CH:22]=[C:21]([F:23])[C:19](=[O:20])[NH:18][C:16]1=[O:17])(=O)C.C[O-].[Na+].[Na]>CO>[F:23][C:21]1[C:19](=[O:20])[NH:18][C:16](=[O:17])[N:15]([CH:22]=1)[C@@H:6]1[O:7][C@H:8]([CH3:14])[C@@H:9]([OH:10])[C@H:5]1[OH:4]

참가 물질

5

반응물 3

HCID 5360545SodiumHCID 10942334Sodium MethoxideHCID 149189135'-Deoxy-5-fluorouridine 2',3'-diacetate

생성물 1

HCID 18343Doxifluridine수율 106.1%

시약·촉매·용매 1

HCID 887Methanol용매2회

반응 조건

온도
0 °C

실험 절차

A solution of 860 g of 1-(5-deoxy-2,3-di-O-acetyl-β-D-ribofuranosyl)-5-fluorouracil in 16 liters of methanol was added to sodium methoxide freshly prepared from 42 g of sodium and 2000 ml of methanol. The methyl acetate resulting during the reaction was removed by repeated concentration of the mixture. The mixture was neutralised by the addition of 1000 ml of a strongly acidic cation exchange resin (H+ -form), freshly washed with methanol. After removing the ion exchange resin, the methanolic solution was concentrated under reduced pressure and the product, which separated in crystalline form, was washed with a mixture, cooled to 0° C., of 1000 ml of methanol and 1000 ml of ethyl acetate. By working-up the mother liquors there was obtained a total of 680 g (97%) of pure 5'-deoxy-5-fluorouridine; m.p. 192°-193° C.; [β]D25 =+139° (c=0.9 in methanol).

후처리

  1. customThe methyl acetate resulting during the reaction was removed
  2. additionThe mixture was neutralised by the addition of 1000 ml of a strongly acidic cation exchange resin (H+ -form)
  3. washfreshly washed with methanol
  4. customAfter removing the ion exchange resin
  5. concentrationthe methanolic solution was concentrated under reduced pressure
  6. customthe product, which separated in crystalline form
  7. washwas washed with a mixture

출처 및 근거

ORD 기록
ord-a5847a422c334566bef67fa7ec849c2d
출처 데이터셋
uspto-grants-1982_07
특허 번호
US04340729

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