Hydrogen Peroxide → HCID 13567851, compound

HRID 1363444Notes

Reaction equation

[C:1]([O:4][C@@H:5]1[C@H:9]([O:10][C:11](=[O:13])[CH3:12])[C@@H:8]([CH2:14][O:15][C:16](=[O:18])[CH3:17])[O:7][C@H:6]1[N:19]1[CH:26]=[CH:25][C:23](=[O:24])[NH:22][C:20]1=[O:21])(=[O:3])[CH3:2].S(=O)(=O)(O)O.[F:32][C:33](I)([F:35])[F:34].OO>[CH-]1C=CC=C1.[CH-]1C=CC=C1.[Fe+2].CS(C)=O>[F:32][C:33]([F:35])([F:34])[C:25]1[C:23](=[O:24])[NH:22][C:20](=[O:21])[N:19]([CH:26]=1)[C@@H:6]1[O:7][C@H:8]([CH2:14][O:15][C:16](=[O:18])[CH3:17])[C@@H:9]([O:10][C:11](=[O:13])[CH3:12])[C@H:5]1[O:4][C:1](=[O:3])[CH3:2]

Participants

Conditions

Temperature: 65 °C

Procedure

0.37 g (1.0 mmol) of 2′,3′,5′-tri-O-acetyluridine 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-2′,3′,5′-tri-O-acetyluridine (19F-NMR yield: 45%) was confirmed by 19F-NMR with 2,2,2-trifluoroethanol as an internal standard. 5-Trifluoromethyl-2′,3′,5′-tri-O-acetyluridine was obtained as a white solid (0.17 g, yield: 40%) 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-1e4476fd29214e33bba90b07029b6f42
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07884202B2

Reaction notes

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