Hydrogen Peroxide → 65499-42-5
Reaction equation
[C:1]([O:4][C@@H:5]1[C@@H:9]([CH2:10][O:11][C:12](=[O:14])[CH3:13])[O:8][C@@H:7]([N:15]2[CH:22]=[CH:21][C:19](=[O:20])[NH:18][C:16]2=[O:17])[CH2:6]1)(=[O:3])[CH3:2].S(=O)(=O)(O)O.[F:28][C:29](I)([F:31])[F:30].OO>[CH-]1C=CC=C1.[CH-]1C=CC=C1.[Fe+2].CS(C)=O>[F:28][C:29]([F:31])([F:30])[C:21]1[C:19](=[O:20])[NH:18][C:16](=[O:17])[N:15]([CH:22]=1)[C@@H:7]1[O:8][C@H:9]([CH2:10][O:11][C:12](=[O:14])[CH3:13])[C@@H:5]([O:4][C:1](=[O:3])[CH3:2])[CH2:6]1Participants
Conditions
- Temperature
- 65 °C
Procedure
0.32 g (1.0 mmol) of 3′,5′-di-O-acetyl-2′-deoxyuridine and 0.058 g (0.3 mmol) of ferrocene were 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: 1.8 ml of dimethyl sulfoxide, 2.0 ml of a 1N dimethyl sulfoxide solution of sulfuric acid, 1.0 ml of a 2.1 mol/l dimethyl sulfoxide solution of trifluoromethyl iodide and 0.2 ml of a 30% hydrogen peroxide aqueous solution. The mixture was stirred at 60 to 70° C. for 20 minutes and then the resulting solution was cooled to room temperature. Formation of 5-trifluoromethyl-3′,5′-di-O-acetyl-2′-deoxyuridine (19F-NMR yield: 75%) was confirmed by 19F-NMR with trifluoroethanol as an internal standard. 5-Trifluoromethyl-3′,5′-di-O-acetyl-2′-deoxyuridine was obtained as a white solid (0.19 g, yield: 50%) 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-7f6e4ad93e3e4c96ad8618809ca4b224
- Source dataset
- uspto-grants-2011_02
- Patent number
- US07884202B2
Reaction notes
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