Adenosine → 2-Amino-9-((2R,3S,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-1H-purin-6(9H)-one

HRID 1682086

Reaktionsgleichung

Reaktionsgleichung von HRID 1682086
[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

Komponenten

4

Edukt 2

HCID 60961AdenosineHCID 460081(2R,3R,4S,5R)-5-(2,6-diaminopurin-9-yl)-4-fluoro-2-(hydroxymethyl)oxolan-3-ol

Produkt 1

HCID 1354349402-Amino-9-((2R,3S,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-1H-purin-6(9H)-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

2,6-Diamino-9-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)-9H-purine (0.1 g, 0.35 mmoles) prepared as in Example 1, was dissolved in 10 ml of water. Calf intestine adenosine deaminase (10 I.U., Boehringer Mannheim) was added and the solution incubated at 37° C. for one day. The solvent was removed under vacuum. The residue was dissolved in acetonitrile/water (85/15) and chromatographed on silica gel with acetonitrile/water (85/15) as the solvent. Product containing fractions were combined and the solvent removed under vacuum. The residue was dissolved in water and lyophilization yielded 0.14 g of the title compound that analysed as a 1.1 hydrate.

Aufarbeitung

  1. customThe solvent was removed under vacuum
  2. dissolutionThe residue was dissolved in acetonitrile/water (85/15)
  3. customchromatographed on silica gel with acetonitrile/water (85/15) as the solvent
  4. additionProduct containing fractions
  5. customthe solvent removed under vacuum
  6. dissolutionThe residue was dissolved in water

Quellen und Nachweise

ORD-Eintrag
ord-6a40a82f62af4dc1b7d291e61a3686bd
Quelldatensatz
uspto-grants-1992_12
Patentnummer
US05175274

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