Cytidine → N4-Acetylcytidine

HRID 2416122Notes

Reaction equation

HRID 2416122 reaction equation
[C@@H:1]1([N:10]2[CH:17]=[CH:16][C:14]([NH2:15])=[N:13][C:11]2=[O:12])[O:9][C@H:6]([CH2:7][OH:8])[C@@H:4]([OH:5])[C@H:2]1[OH:3].[C:18](OC(=O)C)(=[O:20])[CH3:19]>CN(C=O)C>[C:18]([NH:15][C:14]1[CH:16]=[CH:17][N:10]([C@@H:1]2[O:9][C@H:6]([CH2:7][OH:8])[C@@H:4]([OH:5])[C@H:2]2[OH:3])[C:11](=[O:12])[N:13]=1)(=[O:20])[CH3:19]

Participants

4

Reactant 2

HCID 6175CytidineHCID 7918Acetic Anhydride

Product 1

HCID 107461N4-AcetylcytidineYield 100.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of cytidine (1.22 g, 5.00 mmol) in DMF(40 mL) is added acetic anhydride (0.94 mL, 10.00 mmol). The solution is treated with microwave radiation (Panasonic, 1000 Watts) at full power for 40 seconds. The solution is concentrated in vacuo and the residue is co-evaporated with methanol (2×20 mL) to give 4-N-acetyl-cytidine (1.43 g, 95.0%) as a white powder. MS (FAB):m/z 286 (MH+).

Workup

  1. additionThe solution is treated with microwave radiation (Panasonic, 1000 Watts) at full power for 40 seconds
  2. concentrationThe solution is concentrated in vacuo

Sources & evidence

ORD record
ord-204cabac8ed748b38c7d0a581ead5f1d
Source dataset
uspto-grants-2004_11
Patent number
US06822089B1

Reaction notes

Loading…