Adenosine → 2'-Deoxy-2'-fluoroinosine

HRID 37079

Reaction equation

HRID 37079 reaction equation
N[C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[C@@H:11]1[O:16][C@H:15]([CH2:17][OH:18])[C@@H:13]([OH:14])[C@H:12]1[F:19].[C@@H]1(N2C3N=CN=C(N)C=3N=C2)O[C@H](CO)[C@@H](O)[C@H]1[OH:22]>O>[F:19][C@@H:12]1[C@H:13]([OH:14])[C@@H:15]([CH2:17][OH:18])[O:16][C@H:11]1[N:6]1[CH:5]=[N:4][C:3]2[C:2](=[O:22])[NH:10][CH:9]=[N:8][C:7]1=2

Participants

4

Reactant 2

HCID 60961AdenosineHCID 1002532'-Fluoro-2'-deoxyadenosine

Product 1

HCID 1354351722'-Deoxy-2'-fluoroinosine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

6-Amino-9-(2-deoxy-2-fluoro-β-D-ribofuranosyl)-9H-purine (0.29 g, 1.0 mmole), prepared as in Example 8, was dissolved in 100 ml of water. Calf intestinal adenosine deaminase (4 I.U., Boehringer Mannheim) was added and the solution incubated at 37° C. for 24 hrs. The solvent was removed under vacuum. The residue was dissolved in water/n-propanol (7/3) and chromatographed on a 5×90 cm column of Sephadex G-10 (Pharmacia LKB) with water/n-propanol (7/3) as the solvent. 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 hydrate.

Workup

  1. customThe solvent was removed under vacuum
  2. dissolutionThe residue was dissolved in water/n-propanol (7/3)
  3. customchromatographed on a 5×90 cm column of Sephadex
  4. customthe solvent removed under vacuum
  5. dissolutionThe residue was dissolved in water

Sources & evidence

ORD record
ord-24624ba4ad42404e88c2b51eb4f0dcd5
Source dataset
uspto-grants-1995_05
Patent number
US05420115

Linked notes

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