Trifluoroacetic acid → diethyl (E)-2-((2R,3S,4R,5R)-5-(4-benzamido-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-3,4-dihydroxy-tetrahydrofuran-2-yl)vinylphosphonate

Participants

Reaction Steps

Compound 22.4 (163 mg, 0.299 mmol) was treated with TFA (1000 μL) and H2O (100 μL) and stirred at room temperature for 2 h. The solvent was removed in vacuo and the residue was subjected to a silica gel column chromatography eluting with 0-20% MeOH—CH2Cl2 to afford compound 25.1 (65 mg, 43% yield) as a white solid: 1H NMR (CDCl3, 300 MHz) 9.51 (br s, 1H), 8.65 (s, 1H), 8.47 (s, 1H), 7.90 (d, J=7.5 Hz, 2H), 7.51 (t, J=7.5 Hz, 1H), 7.43 (t, J=7.5 Hz, 2H), 6.88 (m, 1H), 6.61 (s, 1H), 5.98 (m, 1H), 4.85 (m, 1H), 4.67 (m, 1H), 4.60 (m, 1H), 3.89 (m, 4H), 1.20 (t, 6H); 31P NMR (CDCl3, 121.4 MHz) 16.6; MS (ESI) m/z 504 [M+H]+.

Provenance & Evidence