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

HRID 2057582Notes

Reaction equation

HRID 2057582 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-bab5abc43c2c408b95c115f7ddb52da4
Source dataset
uspto-grants-1980_07
Patent number
US04211773

Reaction notes

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