Ethylenediaminetetraacetic Acid → 3-hydroxy-6-methyl-2-(2,2,2-trifluoro-1-hydroxy-ethyl)-1H-pyridin-4-one

Participants

Reaction Steps

Proceeding in a similar manner as A, 2-difluoromethyl-5-hydroxy-1-methyl-1H-pyridin-4-one was converted to 6-difluoromethyl-3-hydroxy-1-methyl-2-(2,2,2-trifluoro-1-hydroxy-ethyl)-1H-pyridin-4-one. 1H NMR (DMSO-d6+1 drop of D2O) δ ppm: 7.12 (t, J=52.8 Hz, 1H), 6.56 (s, 1H), 5.83 (b, 1H), 3.79 (s, 3H). 19F NMR (DMSO-d6+1 drop of D2O) δ ppm: −73.3 (3F), −117.8 (2F). MS (m/z) 274.1 [M+1]+. HPLC conditions: Column: XTerra MS C18 5 μm 4.6×250 mm. Mobile phase: A=the aqueous phase: 4 mM Tris, 2 mM EDTA, pH 7.4; B=the organic phase: CH3CN. The gradient program: B %: 0 min. 5%, 15 min. 55%, 25 min. 55%, 25.05 min. 5%, 30 min. 5%. Flow rate=1 ml/min.; injection volume=5 μL; wavelength: 220, 254, 280, 450 nm. Retention time of 2-Difluoromethyl-5-hydroxy-1-methyl-1H-pyridin-4-one=6.7 min. Retention time of 6-difluoromethyl-3-hydroxy-1-methyl-2-(2,2,2-trifluoro-1-hydroxy-ethyl)-1H-pyridin-4-one=11.4 min.

Provenance & Evidence