Hydrochloric Acid → (2R)-4-[5-(2-Fluoro-3-methoxyphenyl)isoxazol-3-yl]-N-hydroxy-2-methyl-2-(methylsulfonyl)butanamide butanamide

Participants

Reaction Steps

Hydrochloric acid (4.0 M in 1,4-dioxane, 0.13 mL, 0.51 mmol, 4 equiv) was added to a solution of (2R)-4-[5-(2-fluoro-3-methoxyphenyl)isoxazol-3-yl]-2-methyl-2-(methylsulfonyl)-N-(tetrahydro-2H-pyran-2-yloxy)butanamide (0.60 g, 0.13 mmol, 1.0 equiv) in 1,4-dioxane-dichloromethane-water (2:2:1, 2.5 mL), and the reaction was allowed to stir at room temperature for 2 h. The solvent was removed under reduced pressure, and the resulting crude material purified by preparative HPLC (Sepax 2-ethyl pyridine 250×21.2 mm 5 μm, heptane-ethanol solvent system as eluent) to provide (2R)-4-[5-(2-Fluoro-3-methoxyphenyl)isoxazol-3-yl]-N-hydroxy-2-methyl-2-(methylsulfonyl)butanamide butanamide (0.01 g, 20%). MS (LCMS) m/z 385.0 (M−1). 1H NMR (400 MHz, METHONAL-d4) δ1.59-1.71 (m, 3H) 2.13-2.29 (m, 1H) 2.61-2.81 (m, 2H) 2.80-2.99 (m, 1H) 3.07 (s, 3H) 3.92 (s, 3H) 6.65-6.84 (m, 1H) 7.16-7.30 (m, 2H) 7.37-7.52 (m, 1H).

Provenance & Evidence