Water → HCID 90387899, compound

Participants

Reaction Steps

To a solution of compound 22 (120 mg, 0.41 mmol) in dried dichloromethane (15 mL) was added DIPEA (130 mg, 1.0 mmol), chloromethyl methyl ether (121 mg, 1.5 mmol), and DMAP (10 mg) at room temperature. After 16 h, water was added and the product extracted into dichloromethane (100 mL×2). The combined extracts were dried, filtered, and removed. The residue was purified by flash column chromatography (silica gel eluted with 10% EtOAc in hexanes) to afford compound 24 (138 mg, 100%): 1H NMR (CDCl3) δ 4.60 (s, 2H), 3.79-3.78 (m, 1H), 3.31 (s, 3H), 0.80 (s, 3H), 0.76 (s, 3H); 13C NMR (CDCl3) δ 220.9, 94.4, 71.5, 55.0, 54.5, 47.7, 45.8, 39.8, 39.6, 36.1, 35.6, 34.7, 33.4, 32.6, 31.7, 28.7, 26.2, 24.1, 23.9, 13.5, 11.3.

Provenance & Evidence