Hydrochloric Acid → (2R)-4-[4-(4-chloro-2-fluorophenyl)-2-oxopyridin-1(2H)-yl]-N-hydroxy-2-methyl-2-(methylsulfonyl)butanamide

Participants

Reaction Steps

(2R)-4-[4-(4-chloro-2-fluorophenyl)-2-oxopyridin-1(2H)-yl]-2-methyl-2-(methylsulfonyl)-N-(tetrahydro-2H-pyran-2-yloxy)butanamide (1188 mg impure material, 1 mmol) was dissolved in 3 mL of dichloromethane. To this solution was added 1 mL of 4M HCl in dioxane and 1 mL of water. The reaction was monitored for completion by LCMS. Upon completion, the reaction mixture was concentrated and redissolved in a minimal amount of dimethylsulfoxide and water and loaded onto a 5g c18 guard-column. This material was purified on a 75g c18 column with 10-40% acetonitrile in water with 0.1% trifluoroacetic acid. The desired material was concentrated yielding 434 mg (88%) of a light yellow solid. LCMS m/z 417.5 (M+1). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.58 (s, 3 H) 2.10-2.23 (m, 1 H) 2.37-2.47 (m, 1 H) 3.11 (s, 3 H) 3.69-3.82 (m, 1 H) 4.04-4.19 (m, 1 H) 6.44-6.52 (m, 1 H) 6.58 (s, 1 H) 7.42 (dd, J=8.29, 1.85 Hz, 1 H) 7.56-7.67 (m, 2 H) 7.77 (d, J=7.02 Hz, 1 H) 11.12 (br. s., 1 H)

Provenance & Evidence