Diiodomethane → Acetic acid (2R,3R,4R,5R)-3,4-diacetoxy-5-(6-chloro-2-iodo-purin-9-YL)-tetrahydro-furan-2-ylmethyl ester

HRID 895099

Reaktionsgleichung

Reaktionsgleichung von HRID 895099
[C:1]([O:4][C@@H:5]1[C@H:9]([O:10][C:11](=[O:13])[CH3:12])[C@@H:8]([CH2:14][O:15][C:16](=[O:18])[CH3:17])[O:7][C@H:6]1[N:19]1[CH:27]=[N:26][C:25]2[C:20]1=[N:21][C:22](N)=[N:23][C:24]=2[Cl:28])(=[O:3])[CH3:2].[I:30]CI.N(OCCCCC)=O>C(#N)C>[C:1]([O:4][C@@H:5]1[C@H:9]([O:10][C:11](=[O:13])[CH3:12])[C@@H:8]([CH2:14][O:15][C:16](=[O:18])[CH3:17])[O:7][C@H:6]1[N:19]1[CH:27]=[N:26][C:25]2[C:20]1=[N:21][C:22]([I:30])=[N:23][C:24]=2[Cl:28])(=[O:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 6346DiiodomethaneHCID 10026Pentyl nitriteHCID 10788628(2R,3R,4R,5R)-2-(Acetoxymethyl)-5-(2-amino-6-chloro-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate

Produkt 1

HCID 482588Acetic acid (2R,3R,4R,5R)-3,4-diacetoxy-5-(6-chloro-2-iodo-purin-9-YL)-tetrahydro-furan-2-ylmethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a solution of (2R,3R,4R,5R)-4-acetyloxy-5-(acetyloxymethyl)-2-(2-amino-6-chloropurin-9-yl)oxolan-3-yl acetate in acetonitrile was added diiodomethane and n-pentyl nitrite. The mixture was heated under nitrogen for 20 hours, then solvent removed under reduced pressure. The residue was purified by chromatography on silica gel, eluting with hexanes to hexanes/ethyl acetate 2:1, to provide (2R,3R,4R,5R)-4-acetyloxy-5-(acetyloxymethyl)-2-(6-chloro-2-iodopurin-9-yl)oxolan-3-yl acetate, which may be recrystallized from ethanol.

Aufarbeitung

  1. temperatureThe mixture was heated under nitrogen for 20 hours
  2. customsolvent removed under reduced pressure
  3. customThe residue was purified by chromatography on silica gel
  4. washeluting with hexanes to hexanes/ethyl acetate 2:1

Quellen und Nachweise

ORD-Eintrag
ord-9ba3d757d3e64f63bac5e5f97322b588
Quelldatensatz
uspto-grants-2005_07
Patentnummer
US06914053B2

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