Ethanol → Cytidine

HRID 1789586Notes

Reaction equation

HRID 1789586 reaction equation
C([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:34]=[CH:33][C:23]([NH:24]C(=O)C2C=CC=CC=2)=[N:22][C:20]1=[O:21])(=O)C.[NH4+].[OH-].C(O)C>CO>[C@@H:6]1([N:19]2[CH:34]=[CH:33][C:23]([NH2:24])=[N:22][C:20]2=[O:21])[O:7][C@H:8]([CH2:14][OH:15])[C@@H:9]([OH:10])[C@H:5]1[OH:4]

Participants

5

Reactant 3

HCID 702EthanolHCID 14923Ammonium HydroxideHCID 13851850HCID 13851850, compound

Product 1

HCID 6175Cytidine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

In methanol (50 ml) is dissolved 2',3',5'-tri-O-acetyl-N4 -benzoylcytidine (0.53 g) followed by addition of concentrated NH4OH (5 ml) with stirring at 70° C. The mixture is stirred at 70° C. for 2.5 hours, at the end of which time ethanol is added. The mixture is allowed to stand at room temperature overnight to give colorless needles of cytidine. Yield 0.26 g (95.6%).

Workup

  1. additionis added

Sources & evidence

ORD record
ord-2131771375784b5dbff2e1c2b9f89ab5
Source dataset
uspto-grants-1987_08
Patent number
US04689404

Reaction notes

Loading…