HCID 54119678, compound → 2'-Fluoro-5-bromo-1-beta-D-arabinofuranosylcytosine

HRID 1981884Notes

Reaction equation

HRID 1981884 reaction equation
C([O:4][C@@H:5]1[C@@H:9]([CH2:10][O:11]C(=O)C2C=CC=CC=2)[O:8][C@@H:7]([N:20]2[CH:27]=[C:26]([Br:28])[C:24]([NH2:25])=[N:23][C:21]2=[O:22])[C@H:6]1[F:29])(=O)C>N>[F:29][C@H:6]1[C@H:5]([OH:4])[C@@H:9]([CH2:10][OH:11])[O:8][C@H:7]1[N:20]1[CH:27]=[C:26]([Br:28])[C:24]([NH2:25])=[N:23][C:21]1=[O:22]

Participants

3

Reactant 1

HCID 54119678HCID 54119678, compound

Product 1

HCID 1723922'-Fluoro-5-bromo-1-beta-D-arabinofuranosylcytosineYield 81.3%

Reagents, catalysts & solvents 1

HCID 222AmmoniaSolvent

Procedure

1-(3-O-Acetyl-5-O-benzoyl-2-deoxy-2-fluoro-β-D-arabinofuranosyl)-5-bromocytosine (1.0 g) is dissolved in saturated methanolic ammonia (100 ml) and the solution is left standing for 24 hours at room temperature. The solvent is removed in vacuo and the residue was crystallized from ethanol to give 560 mg of 1-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)-5-bromocytosine, m.p. 201°-202°.

Workup

  1. waitthe solution is left
  2. customThe solvent is removed in vacuo
  3. customthe residue was crystallized from ethanol

Sources & evidence

ORD record
ord-f16d908274074347954bd7d6e9b1f9ae
Source dataset
uspto-grants-1986_06
Patent number
US04594339

Reaction notes

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