Hydrogen Peroxide → 5-Trifluoromethyl-2'-deoxycytidine
Reaction equation
[C@@H:1]1([N:9]2[CH:16]=[CH:15][C:13]([NH2:14])=[N:12][C:10]2=[O:11])[O:8][C@H:5]([CH2:6][OH:7])[C@@H:3]([OH:4])[CH2:2]1.S(=O)(=O)(O)O.[F:22][C:23](I)([F:25])[F:24].OO>S([O-])([O-])(=O)=O.[Fe+2].CS(C)=O>[F:22][C:23]([F:25])([F:24])[C:15]1[C:13]([NH2:14])=[N:12][C:10](=[O:11])[N:9]([CH:16]=1)[C@@H:1]1[O:8][C@H:5]([CH2:6][OH:7])[C@@H:3]([OH:4])[CH2:2]1Participants
Conditions
- Temperature
- 45 °C
Procedure
0.15 g (1.0 mmol) of 2′-deoxycytidine 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: 2.0 ml of dimethyl sulfoxide, 2.0 ml of a 1N dimethyl sulfoxide solution of sulfuric acid, 1.0 ml of a 3.0 mol/l dimethyl sulfoxide solution of trifluoromethyl iodide, 0.2 ml of a 30% hydrogen peroxide aqueous solution and 0.3 ml of a 1.0 mol/l aqueous solution of iron (II) sulfate. 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-trifluoromethyl-2′-deoxycytidine (19F-NMR yield: 11%) was confirmed by 19F-NMR with 2,2,2-trifluoroethanol as an internal standard. 5-Trifluoromethyl-2′-deoxycytidine was obtained as a white solid (0.01 g, yield: 3.3%) by column chromatography.
Workup
- customplaced in a 50 ml two-neck flask
- customequipped with a magnetic rotor
- additionThe following materials were added
- temperaturethe resulting solution was cooled to room temperature
Sources & evidence
- ORD record
- ord-be673d4b693d4459b1ad367fff6c66d1
- Source dataset
- uspto-grants-2011_02
- Patent number
- US07884202B2
Reaction notes
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