Cesium carbonate → HCID 10357872, compound

Participants

Reaction Steps

A solution of Example 22B (0.102 g, 0.31 mmol), cesium carbonate (0.111 g, 0.34 mmol), and chloromethyl pivalate (0.055 mL, 0.38 mmol) in DMF (3 mL) at room temperature was stirred for 24 hours, diluted with ethyl acetate, washed sequentially with water, aqueous NaHCO3, pH 7 buffer, and brine, dried (MgSO4), filtered, and concentrated. The residue was dissolved in 4M HCl in dioxane (2 mL), stirred for 1 hour, treated with water (1 mL), stirred for 1 hour, concentrated, and purified by reverse phase HPLC with acetonitrile/water to provide the desired product. MS (ESI) m/e 308 (M+H)+; 1H NMR (300 MHz, DMSO-d6) δ 7.87–7.80 (br s, 2H), 6.53 (m, 0.7H), 6.33 (d, 0.3H), 4.40 (m, 0.3H), 4.24 (m, 0.7H), 4.28 (s, 0.6H), 4.26 (s, 1.4H), 3.53 (m, 1H), 2.63 (m, 2H), 2.48 (m, 2H), 1.90–1.75 (m, 2H), 1.22–1.16 (m, 12H).

Provenance & Evidence