Water → Levovirin

HRID 478765

Reaktionsgleichung

Reaktionsgleichung von HRID 478765
C(O[C@H]1[C@@H](OC(=O)C)[C@H](COC(=O)C)O[C@@H]1N1C=NC(C(OC)=O)=N1)(=O)C.O.[CH:29]1[N:33]([C@@H:34]2[O:38][C@H:37]([CH2:39][OH:40])[C@@H:36]([OH:41])[C@H:35]2[OH:42])[N:32]=[C:31]([C:43]([NH2:45])=[O:44])[N:30]=1>CO.N>[C@H:34]1([N:33]2[CH:29]=[N:30][C:31]([C:43]([NH2:45])=[O:44])=[N:32]2)[O:38][C@@H:37]([CH2:39][OH:40])[C@H:36]([OH:41])[C@@H:35]1[OH:42]

Komponenten

5

Edukt 3

HCID 962Water2×HCID 37542RibavirinHCID 10691464Methyl 1-(2,3,5-Tri-O-acetyl-beta-L-ribofuranosyl)-1,2,4-triazole-3-carboxylate

Produkt 1

HCID 460516Levovirin

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21705897Ammonia methanolLösungsmittel

Versuchsvorschrift

The substrate (20) (1.1 g) was dissolved in CH3OH/NH3 at 0° C. and placed in a steel bomb. The bomb was closed and stirred at room temperature for 18 h. The steel bomb was cooled, opened and evaporated to dryness. The residue was tried to crystallization with little ethanol. The product crystallized, but on filtration, the crystals re-absorbed water and became a paste. The crystallization repeated several times. Finally it crystallized from Methanol/Ethanol mixture. The colorless crystals was filtered, washed with methanol and dried in vacuo. The filtrate was evaporated again which on standing gave further crystals. Total yield 0.5 g (72%); mp: 177-179° C.; [a]D=+38.33 (c 3 mg/mL H2O); D form of Ribavirin [a]D=−36.0 (c 3.0 mg/mL H2O); 1H NMR (Me2SO-d6) δ3.46 (m, 1H, C5′H), 3.60 (m, 1H, C5′H), 3.92 (q, 1H, C4′H), 4.12 (q, 1H), 4.34 (q, 1H), 4.88 (t, 1H, C5′OH), 5.20 (d, 1H), 5.58 (d, 1H), 5.80 (d, 1H, C1′H), 7.60 (bs, 1H, NH), 7.82 (bs, 1H, NH), and 8.82 (s, 1H, C3H). Anal. Calc. for C8H12N4O5 (244.20): C, 39.34; H, 4.95; N, 22.94. Found: C, 39.23; H, 4.97; N, 22.91.

Aufarbeitung

  1. customThe bomb was closed
  2. customevaporated to dryness
  3. customThe residue was tried to crystallization with little ethanol
  4. customThe product crystallized
  5. filtrationon filtration
  6. customthe crystals re-absorbed water
  7. customThe crystallization
  8. customFinally it crystallized from Methanol/Ethanol mixture
  9. filtrationThe colorless crystals was filtered
  10. washwashed with methanol
  11. customdried in vacuo
  12. customThe filtrate was evaporated again which on standing
  13. customgave further crystals

Quellen und Nachweise

ORD-Eintrag
ord-c12569e003e54a7d975e03becb11dbea
Quelldatensatz
uspto-grants-2003_11
Patentnummer
US06642206B2

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