Acetic Acid → 2-Fluoro-9-(alpha-L-lyxofuranosyl)-9H-purin-6-amine

HRID 1724624Notes

Reaction equation

HRID 1724624 reaction equation
[F:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[C@@H:11]2[O:33][C@@H:32]([CH2:34][O:35]C(=O)C3C=CC=CC=3)[C@@H:22]([O:23]C(=O)C3C=CC=CC=3)[C@H:12]2[O:13]C(=O)C2C=CC=CC=2)=[C:4]([NH2:44])[N:3]=1.[OH-].[K+].C(O)(=O)C>C(O)C>[F:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[C@@H:11]2[O:33][C@@H:32]([CH2:34][OH:35])[C@@H:22]([OH:23])[C@H:12]2[OH:13])=[C:4]([NH2:44])[N:3]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 14797Potassium HydroxideHCID 690770502-Fluoro-9-(2,3,5-tri-O-benzoyl-alpha-L-lyxofuranosyl)-9H-purin-6-amine

Product 1

HCID 161295862-Fluoro-9-(alpha-L-lyxofuranosyl)-9H-purin-6-amine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A suspension of 1a (108 mg, 0.18 mmol) in ethanol (10 ml) at room temperature is treated in one portion with 0.50 M KOH (anhydrous powder) in ethanol (180 μl). The mixture is stirred 5 h, neutralized with glacial acetic acid (6 μl), and evaporated to dryness. The resulting residue is crystallized from 1:1 acetonitrile/water to afford pure (1b) as a white solid.

Workup

  1. customevaporated to dryness
  2. customThe resulting residue is crystallized from 1:1 acetonitrile/water

Sources & evidence

ORD record
ord-54d163ba2d144dcf82559fa6052010a7
Source dataset
uspto-grants-2009_02
Patent number
US07488598B2

Reaction notes

Loading…