Thymidine → 6-(Cyclopropylamino)-9-(2-deoxy-2-fluoro-beta-D-ribofuranosyl)-9H-purine

HRID 37075

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HRID 37075 반응식
[CH:1]1([NH:4][C:5]2[N:13]=[CH:12][N:11]=[C:10]3[C:6]=2[N:7]=[CH:8][NH:9]3)[CH2:3][CH2:2]1.[F:14][C@@H:15]1[C@H:19]([OH:20])[C@@H:18]([CH2:21][OH:22])[O:17][C@H:16]1N1C=CC(=O)NC1=O.[N-]=[N+]=[N-].[K+].[OH-].[K+].[C@@H]1(N2C=C(C)C(=O)NC2=O)O[C@H](CO)[C@@H](O)C1.C1(NC2N=C3C(NC=N3)=CN=2)CC1.[NH4+].[OH-]>P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[CH:1]1([NH:4][C:5]2[N:13]=[CH:12][N:11]=[C:10]3[C:6]=2[N:7]=[CH:8][N:9]3[C@@H:16]2[O:17][C@H:18]([CH2:21][OH:22])[C@@H:19]([OH:20])[C@H:15]2[F:14])[CH2:3][CH2:2]1

참가 물질

10

반응물 8

HCID 5789Thymidine3회HCID 14797Potassium Hydroxide2회HCID 14923Ammonium HydroxideHCID 1508512'Fluoro-2'-deoxyuridineHCID 10290740Potassium azideHCID 113098196-(Cyclopropylamino)-9H-purineHCID 67535543(Cyclopropylamino) purineHCID 178420900HCID 178420900, 화합물

생성물 1

HCID 100409666-(Cyclopropylamino)-9-(2-deoxy-2-fluoro-beta-D-ribofuranosyl)-9H-purine

시약·촉매·용매 1

HCID 62657Potassium Phosphate, Tribasic용매

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온도
37 °C

실험 절차

6-(Cyclopropylamino)-9H-purine (0.2 g, 1.1 mmoles) and 1-(2-deoxy-2-fluoro-β-D-ribofuranosyl)uracil (0.4 g, 1.6 mmoles) which may be prepared according to J. F. Codington et al. (J. Org. Chem. 29:558, 1964) were suspended in 20 ml of 5 mM potassium phosphate buffer, pH 7.0, which contained 0.04% (w/v) potassium azide. The pH of the suspension was adjusted to 7.0 with KOH. Thymidine phosphorylase (2,000 I.U.) and purine nucleoside phosphorylase (5,540 I.U.) (T. A. Krenitsky et al., Biochemistry 20:3615, 1981 and U.S. Pat. No. 4,381,344) were added and the suspension stirred at 37° C. On day 5, 0.2 g of 6-(cyclopropylamino)purine and 2,000 I.U. of thymidine phosphorylase and 5,540 I.U. of purine nucleoside phosphorylase were added. On day 9, 0.2 g of 6 (cyclopropylamino) purine was added and the pH of the reaction was adjusted to 7.0 with KOH. Thymidine phosphorylase (2,000 I.U.) and purine nucleoside phosphorylase (5,540 I.U.) were added. On day 20, the pH of the reaction was adjusted to 9.4 with NH4OH and the reaction was applied to a 2.5×8.5 cm column of anion exchange resin (Bio-Rad AG1X2-hydroxide form). After washing with water, the product was eluted with water/methanol (7/3). Product-containing fractions were combined and the solvent removed under vacuum. The residue was dissolved in water and lyophilized to obtain title compound that analyzed as a 0.4 hydrate.

후처리

  1. addition4,381,344) were added
  2. waitOn day 20
  3. washAfter washing with water
  4. washthe product was eluted with water/methanol (7/3)
  5. customthe solvent removed under vacuum
  6. dissolutionThe residue was dissolved in water

출처 및 근거

ORD 기록
ord-1774b0714a6f42688356dd52b53265b5
출처 데이터셋
uspto-grants-1995_05
특허 번호
US05420115

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