Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 45110125, compound

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Reaction Steps

A solution of N-{3-[(S)-1,1-Dimethyl-2-(tetrahydro-pyran-2-yloxy)-propyl]-isoxazol-5-yl}-2-methyl-2-(tetrahydro-pyran-4-sulfonyl)-propionamide (1.14 g, 2.41 mmol) and pyridinium p-toluenesulfonate (120.63 mg, 0.48 mmol) in ethanol (11 mL) is stirred at 65° C. for 3 h. After this time, the reaction mixture is concentrated under reduced pressure and partitioned between ethyl acetate and water. The layers are separated and the aqueous layer is extracted with ethyl acetate once. The organic extracts are combined and washed with brine, dried over Na2SO4, filtered and concentrated. The resulting solid is trituated in ethanol and filtered to yield the title compound. Yield 76.4%; (400 MHz, CHLOROFORM-d) δ ppm 1.15 (3H, d), 1.28 (6H, s), 1.72 (6H, s), 1.80-1.90 (2H, m), 1.90-2.02 (2H, m), 2.26 (1H, d), 3.32-3.43 (2H, m), 3.40-3.50 (1H, m), 3.85-3.93 (1H, m), 4.00-4.10 (2H, m), 6.29 (1H, s), 9.62 (1H, s). ES-MS: m/z 389 [M+H].

Provenance & Evidence