Cytidine → N4-Acetylcytidine

HRID 2393720Notes

Reaction equation

HRID 2393720 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)C=O>[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-Acetylcytidine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Cytidine (1) (7.3 g, 30 mmoles) was suspended in anhydrous N,N-dimethylformamide (120 ml) and to it was added acetic anhydride (3.12 ml, 33 mmoles). The mixture was stirred at room temperature overnight. After removal of the DMF under reduced pressure, the resulting residue was triturated with excess of diethylether (~30 ml) and the crystalline product obtained collected by filtration, washed thoroughly with diethylether and air dried to get a quantitative yield of 2. A small portion was crystallized from ethanol/water mixture (1:1) to obtain crystals for analytical purposes.

Workup

  1. customAfter removal of the DMF under reduced pressure
  2. customthe resulting residue was triturated with excess of diethylether (~30 ml)
  3. customthe crystalline product obtained
  4. filtrationcollected by filtration
  5. washwashed thoroughly with diethylether and air
  6. customdried

Sources & evidence

ORD record
ord-9dbb90c2d279425796ee1fee43f18ee9
Source dataset
uspto-grants-1998_09
Patent number
US05808039

Reaction notes

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