Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 66558121, compound

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Reaction Steps

To a solution of (2R)-4-(4-cyclohexyl-1H-pyrazol-1-yl)-2-methyl-2-(methylsulfonyl)-N-(tetrahydro-2H-pyran-2-yloxy)butanamide (260 mg, 0.608 mmol, 1 eq) in EtOH (6 mL), was added PPTS (45.7 mg, 0.182 mmol, 0.3 eq), and the reaction mixture was heated at reflux overnight. The crude product mixture was purified by reverse phase HPLC (Column: Phenomenex Gemini NX 150×21.2 mm 5μ; Flow rate 28 mL/min; conditions: 5-95% Water/MeOH containing 0.1% NH4OH) to give (2R)-4-(4-cyclohexyl-1H-pyrazol-1-yl)-N-hydroxy-2-methyl-2-(methylsulfonyl)butanamide (137 mg, 65% yield). 1H NMR (400 MHz, DMSO-d6) δ 7.48 (s, 1H), 7.25 (s, 1H), 4.13-4.03 (m, 1H), 3.97-3.85 (m, 1H), 3.02 (s, 3H), 2.68-2.57 (m, 1H), 2.43-2.33 (m, 1H), 2.21-2.08 (m, 1H), 1.89-1.80 (m, 1H), 1.74-1.57 (m, 3H), 1.42 (s, 3H), 1.25 (s, 6H). LC-MS M+H+344.1.

Provenance & Evidence