6-Azido-2-fluoro-9-(2,3,5-tri-O-benzyl-beta-D-arabinofuranosyl)purine → Fludarabine

HRID 1646667

반응식

HRID 1646667 반응식
[N:1]([C:4]1[N:12]=[C:11]([F:13])[N:10]=[C:9]2[C:5]=1[N:6]=[CH:7][N:8]2[C@@H:14]1[O:34][C@H:33]([CH2:35][O:36]CC2C=CC=CC=2)[C@@H:24]([O:25]CC2C=CC=CC=2)[C@@H:15]1[O:16]CC1C=CC=CC=1)=[N+]=[N-]>COCCO.[Pd](Cl)Cl>[C@@H:14]1([N:8]2[CH:7]=[N:6][C:5]3[C:9]2=[N:10][C:11]([F:13])=[N:12][C:4]=3[NH2:1])[O:34][C@H:33]([CH2:35][OH:36])[C@@H:24]([OH:25])[C@@H:15]1[OH:16]

참가 물질

4

반응물 1

HCID 544897616-Azido-2-fluoro-9-(2,3,5-tri-O-benzyl-beta-D-arabinofuranosyl)purine

생성물 1

HCID 657237Fludarabine수율 67.6%

시약·촉매·용매 2

HCID 24290Palladium Chloride촉매HCID 80192-Methoxyethanol용매

실험 절차

6-Azido-2-fluoro-9-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)purine (0.19 g) was dissolved in 2-methoxyethanol (20 mL) with palladium (II) chloride (PdCl2) (20 mg) and activated carbon and the mixture was hydrogenated at 55 pounds per square inch (psi) in a Parr shaker. The reaction was monitored by thin layer chromatography (TLC) until complete. The mixture was then filtered through celite and the filtrate was concentrated in vacuo. Three times, the residue was dissolved in ethanol and reconcentrated. Then the residue was recrystalized from ethanol/water to obtain 0.063 g of the title compound which was consistent in its structure with an authentic sample by IR and TLC.

후처리

  1. filtrationThe mixture was then filtered through celite
  2. concentrationthe filtrate was concentrated in vacuo
  3. dissolutionThree times, the residue was dissolved in ethanol
  4. customThen the residue was recrystalized from ethanol/water

출처 및 근거

ORD 기록
ord-4d0b759483994145a1322818e9484f05
출처 데이터셋
uspto-grants-1993_01
특허 번호
US05180824

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