Water → Levovirin

HRID 366944

反応式

HRID 366944 の反応式
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]

参加物

5

反応物 3

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

生成物 1

HCID 460516Levovirin

試薬・触媒・溶媒 1

HCID 21705897Ammonia methanol溶媒

実験手順

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) δ 3.46 (m, 1H, C5'H), 3.60 (m, 1H, C5 h), 3.92 (q, 1H, C4H), 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.

後処理

  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

出典と根拠

ORDレコード
ord-da18caa43eef453bb8307b04446faa21
出典データセット
uspto-grants-2000_10
特許番号
US06130326

関連ノート

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