Hydrochloric Acid → (R)-N-hydroxy-2-methyl-2-(methylsulfonyl)-4-(2-oxo-4-(phenylethynyl) pyridin-1(2H)-yl)butanamide

Participants

Reaction Steps

A solution of 1.0 M aqueous HCl (10 ml) was added slowly to a solution of (2R)-2-methyl-2-(methylsulfonyl)-4-(2-oxo-4-(phenylethynyl)pyridin-1(2H)-yl)-N-(tetrahydro-2H-pyran-2-yloxy)butanamide (107 mg, 0.226 mmol) in 1,4-dioxane (20 mL) at room temperature. The reaction mixture was allowed to stir at room temperature overnight. After 18 hours the reaction was concentrated to low volume then redissolved in methanol (20 ml) and concentrated in vacuo to afford a light-yellow solid. Yield 71 mg, 81%. MS (APCI) m/z 389.4 (M+H), 1H NMR (400 MHz, DMSO-d6) δ ppm 1.46 (none, 3 H) 1.53 (s, 3 H) 2.03-2.17 (m, 1 H) 2.33-2.45 (m, 1 H) 3.07 (s, 3 H) 3.71 (td, J=11.90, 4.88 Hz, 1 H) 3.96-4.14 (m, 1 H) 6.35 (dd, J=6.93, 1.85 Hz, 1 H) 6.56 (d, J=1.76 Hz, 1 H) 7.36-7.48 (m, 3 H) 7.51-7.61 (m, 2 H) 7.69 (d, J=7.02 Hz, 1 H) 11.05 (br. s., 1 H)

Provenance & Evidence