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

HRID 1906365Notes

Reaction equation

HRID 1906365 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

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.;

Workup

  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

Sources & evidence

ORD record
ord-bc47172fb9ed4514ba1b937dbe8be275
Source dataset
uspto-grants-1987_03
Patent number
US04652554

Reaction notes

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