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

HRID 1646667

反応式

HRID 1646667 の反応式
[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]

参加物

4

反応物 1

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

生成物 1

HCID 657237Fludarabine収率 67.6%

試薬・触媒・溶媒 2

HCID 24290Palladium Chloride触媒HCID 80192-Methoxyethanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-4d0b759483994145a1322818e9484f05
出典データセット
uspto-grants-1993_01
特許番号
US05180824

関連ノート

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