Water → 1-(2-O-Nitro-beta-D-arabinofuranosyl)cytosine

HRID 1906365노트

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HRID 1906365 반응식
[N+:1]([O:4][C@H:5]1[C@H:9]([O:10]C(=O)C)[C@@H:8]([CH2:14][O:15]C(=O)C)[O:7][C@H:6]1[N:19]1[CH:29]=[CH:28][C:23]([NH:24]C(=O)C)=[N:22][C:20]1=[O:21])([O-:3])=[O:2].C[O-].[Ba+2].C[O-].O>CO>[N+:1]([O:4][C@H:5]1[C@H:9]([OH:10])[C@@H:8]([CH2:14][OH:15])[O:7][C@H:6]1[N:19]1[CH:29]=[CH:28][C:23]([NH2:24])=[N:22][C:20]1=[O:21])([O-:3])=[O:2]

참가 물질

5

반응물 3

HCID 962WaterHCID 13438163Barium methanolateHCID 138234091-(2-O-nitro-3,5-di-O-acetyl-beta-D-arabinofuranosyl)-N4-acetylcytosine

생성물 1

HCID 1343641-(2-O-Nitro-beta-D-arabinofuranosyl)cytosine수율 86.3%

시약·촉매·용매 1

HCID 887Methanol용매2회

실험 절차

To a solution of 1-(2-O-nitro-3,5-di-O-acetyl-β-D-arabinofuranosyl)-N4 -acetylcytosine (10 g., 24 mmol) in anhydrous methanol (425 ml) under an atmosphere of dry nitrogen was added 1.9N barium methoxide (5 ml., 9.5 meq) in methanol. The reaction mixture was stirred at room temperature under an inert atmosphere for one hour and was then neutralized with a cation exchange resin (90 g., Bio-Rex 70/H+, 100-200 mesh )in the presence of water (5 ml). The resin was separated by filtration and washed with methanol. The combined filtrate and washings were evaporated under reduced pressure to yield crude 1-(2-O-nitro-β-D-arabinofuranosyl)cytosine (6.60 g., 95%), which was crystallized from H2O to yield pure 1-(2-O-nitro-β-D-arabinofuranosyl)cytosine (5.97 g., 86%): m.p. 151.3°-152.7° C.;

후처리

  1. customThe resin was separated by filtration
  2. washwashed with methanol
  3. customThe combined filtrate and washings were evaporated under reduced pressure
  4. customto yield crude 1-(2-O-nitro-β-D-arabinofuranosyl)cytosine (6.60 g., 95%), which
  5. customwas crystallized from H2O

출처 및 근거

ORD 기록
ord-bc47172fb9ed4514ba1b937dbe8be275
출처 데이터셋
uspto-grants-1987_03
특허 번호
US04652554

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