Adenosine → 2'-Deoxy-2'-fluoroguanosine

HRID 37068

Reaction equation

HRID 37068 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[C@@H:11]2[O:16][C@H:15]([CH2:17][OH:18])[C@@H:13]([OH:14])[C@H:12]2[F:19])=[C:4](N)[N:3]=1.[C@@H]1(N2C3N=CN=C(N)C=3N=C2)O[C@H](CO)[C@@H](O)[C@H]1[OH:23]>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:8]1[CH:7]=[N:6][C:5]2[C:4](=[O:23])[NH:3][C:2]([NH2:1])=[N:10][C:9]1=2

Participants

4

Reactant 2

HCID 60961AdenosineHCID 99711012-Amino-2'-deoxy-2'-fluoroadenosine

Product 1

HCID 1354155652'-Deoxy-2'-fluoroguanosine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
4 °C

Procedure

2,6-Diamino-9-(2-deoxy-2-fluoro-β-D-ribofuranosyl)-9H-purine (0.20 g, 0.64 mmole), prepared as in Example 6, was dissolved in 15 ml of water. Calf intestinal adenosine deaminase (4 I.U., Boehringer Mannheim) was added and the solution incubated at 37° for 4 days. The solution was cooled to 4° C. After 3 hrs, the suspension was filtered to remove the first batch of product crystals. The volume of the filtrate was reduced under vacuum and the suspension cooled to 4° C. The suspension was filtered to remove the second batch of product crystals. The batches of product crystals were combined, suspended in water and lyophilized to obtain title compound that analyzed as a 1.3 hydrate.

Workup

  1. waitAfter 3 hrs
  2. filtrationthe suspension was filtered
  3. customto remove the first batch of product crystals
  4. temperaturethe suspension cooled to 4° C
  5. filtrationThe suspension was filtered
  6. customto remove the second batch of product crystals

Sources & evidence

ORD record
ord-7aa613c29b004721978c946d018d6d83
Source dataset
uspto-grants-1995_05
Patent number
US05420115

Linked notes

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