Trifluoroacetic acid → HCID 67034300, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of (S)-di-tert-butyl (3-(2-fluoro-4-(5-(2-oxo-4-(pyridin-2-yl)oxazolidin-3-yl)pyrazolo[1,5-a]pyrimidin-3-yl)phenyl)-1H-1,2,4-triazol-1-yl)methyl phosphate (50 mg, 0.075 mmol) in DCM (0.5 mL) cooled to 0° C. was added TFA (0.1 mL) and the reaction stirred at 0° C. for 1 hour. The reaction was concentrated under vacuum and azeotroped with DCM/Hexanes. The remaining material was taken up in water. The aqueous layer was made basic (pH 9) by the addition of saturated NaHCO3. HCl (0.1 N) was then slowly added to the solution to adjust the pH to 2. The precipitated solid was collected by filtration, washed with acetone and diethyl ether, and dried under vacuum to give (S)-(3-(2-fluoro-4-(5-(2-oxo-4-(pyridin-2-yl)oxazolidin-3-yl)pyrazolo[1,5-a]pyrimidin-3-yl)phenyl)-1H-1,2,4-triazol-1-yl)methyl dihydrogen phosphate (22 mg, 53% yield) as a yellow solid. 1H-NMR (400 MHz, DMSO-d6) δ 9.11 (d, J=7.6 Hz, 1H), 8.79 (s, 1H), 8.73 (s, 1H), 8.52 (d, J=4.0 Hz, 1H), 7.99 (m, 2H), 7.84 (t, J=7.6 Hz, 1H), 7.72 (m, 3H), 7.31 (t, J=6.4 Hz, 1H), 6.06 (d, J=6.0 Hz, 1H), 5.95 (d, J=10.8 Hz, 2H), 4.91 (t, J=8.4 Hz, 1H), 4.32 (dd, J=8.4 Hz, 2.8 Hz, 1H).

Provenance & Evidence