Hydrogen Peroxide → HCID 510990, compound

HRID 1363449Notes

Reaction equation

HRID 1363449 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].[F:18][C:19](I)([F:21])[F:20].OO>S([O-])([O-])(=O)=O.[Fe+2].CS(C)=O>[F:18][C:19]([F:21])([F:20])[C:16]1[C:14]([NH2:15])=[N:13][C:11](=[O:12])[N:10]([CH:17]=1)[C@@H:1]1[O:9][C@H:6]([CH2:7][OH:8])[C@@H:4]([OH:5])[C@H:2]1[OH:3]

Participants

6

Reactant 3

HCID 784Hydrogen PeroxideHCID 6175CytidineHCID 16843Trifluoroiodomethane

Product 1

HCID 510990HCID 510990, compoundYield 24%

Reagents, catalysts & solvents 2

HCID 24393Ferrous SulfateCatalystHCID 679Dimethyl SulfoxideSolvent2×

Conditions

Temperature
45 °C

Procedure

0.24 g (1.0 mmol) of cytidine was weighed and placed in a 50 ml two-neck flask equipped with a magnetic rotor and the atmosphere in the flask was replaced with argon. The following materials were added thereinto: 4.0 ml of dimethyl sulfoxide, 1.0 ml of a 3.0 mol/l dimethyl sulfoxide solution of trifluoromethyl iodide, 0.3 ml of a 1.0 mol/l aqueous solution of iron (II) sulfate and 0.2 ml of a 30% hydrogen peroxide aqueous solution. The mixture was stirred at 40 to 50° C. for 20 minutes and then the resulting solution was cooled to room temperature. Formation of 5-trifluoromethylcytidine (19F-NMR yield: 24%) was confirmed by 19F-NMR with 2,2,2-trifluoroethanol as an internal standard. 5-Trifluoromethylcytidine was obtained (0.034 g, yield: 11%) by column chromatography.

Workup

  1. customplaced in a 50 ml two-neck flask
  2. customequipped with a magnetic rotor
  3. additionThe following materials were added
  4. temperaturethe resulting solution was cooled to room temperature

Sources & evidence

ORD record
ord-ce8abc8ff1534555afb35523cfd9598d
Source dataset
uspto-grants-2011_02
Patent number
US07884202B2

Reaction notes

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