Cesium carbonate → 4-chloro-N-((1R,2R)-2-(hydroxymethyl)cyclohexyl)-N-(4-(oxazol-2-yl)benzyl)benzenesulfonamide

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Reaction Steps

The title compound was synthesized from 4-chloro-N-((1R,2R)-2-(hydroxymethyl)cyclohexyl)benzenesulfonamide (100 mg, 0.33 mmol), cesium carbonate (129 mg, 0.40 mmol), and 2-(4-(bromomethyl)phenyl)oxazole (94 mg, 0.40 mmol) according to the procedure described for 4-chloro-N-(2,3-difluoro-4-(oxazol-2-yl)benzyl)-N-((1R,2R)-2-(hydroxymethyl)cyclohexyl)benzenesulfonamide (Example 20) to give 4-chloro-N-((1R,2R)-2-(hydroxymethyl)cyclohexyl)-N-(4-(oxazol-2-yl)benzyl)benzenesulfonamide (21 mg, 13%). 1H NMR (400 MHz, CDCl3) δ ppm 7.98 (d, J=8.31 Hz, 2H), 7.70 (d, J=8.00 Hz, 3H), 7.43-7.51 (m, 4H), 7.23 (s, 1H), 4.73 (d, J=15.11 Hz, 1H), 4.09 (d, J=15.00 Hz, 1H), 3.66-3.81 (m, 2H), 3.07 (t, J=10.83 Hz, 1H), 2.62 (br. s., 1H), 1.62-1.73 (m, 1H), 1.37-1.62 (m, 4H), 1.06-1.28 (m, 2H), 0.81-1.06 (m, 2H). Analytical HPLC R.T.=22.99 min. MS [M+H]+=461. HRMS [M+H]+ calc'd 461.1302, found 461.1283. Chiral LC: R.T.=18.97 min., >98% ee.

Provenance & Evidence