Hydrochloric Acid → (2R)-4-(4-cyano-1H-pyrazol-1-yl)-N-hydroxy-2-methyl-2-(methylsulfonyl)butanamide

Participants

Reaction Steps

To a solution of (2R)-4-(4-cyano-1H-pyrazol-1-yl)-2-methyl-2-(methylsulfonyl)-N-(tetrahydro-2H-pyran-2-yloxy)butanamide (0.165 g, 0.445 mmol) in EtOH (20 mL) was added HCl (1 M solution, 5 mL). The reaction mixture was allowed to stir at room temperature overnight. The reaction mixture was concentrated and was purified via reverse-phase chromatography system, using 5%-95% acetonitrile/water with 0.1% formic acid modifier as the gradient elution solvent. Target fractions were combined and evaporated to yield (2R)-4-(4-cyano-1H-pyrazol-1-yl)-N-hydroxy-2-methyl-2-(methylsulfonyl)butanamide (21 mg, 16% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 1.47 (s, 3H), 2.16-2.33 (m, 1H), 2.59-2.80 (m, 1H), 3.04 (s, 3H), 3.96-4.17 (m, 1H), 4.18-4.39 (m, 1H), 8.05 (s, 1H) 8.57 (s, 1H), 9.24 (br. s., 1H) 10.97 (br. s., 1H). LC-MS M−H 285.3.

Provenance & Evidence