Water → Levovirin

HRID 1368708

반응식

HRID 1368708 반응식
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]

참가 물질

5

반응물 3

HCID 962Water2회HCID 37542RibavirinHCID 10691464Methyl 1-(2,3,5-Tri-O-acetyl-beta-L-ribofuranosyl)-1,2,4-triazole-3-carboxylate

생성물 1

HCID 460516Levovirin

시약·촉매·용매 1

HCID 21705897Ammonia methanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-8807b8b667ca42159a66b17b2f106330
출처 데이터셋
uspto-grants-2003_06
특허 번호
US06573248B2

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