Isopropyl iodide → HCID 69232462, compound

Participants

Reaction Steps

A solution of 3-[4-{2-[2-(4-hydroxy-phenyl)-5-methyl-oxazol-4-yl]-ethoxy}-2-(isopropoxycarbonylamino-methyl)-phenyl]-propionic acid tert-butyl ester (300 mg, 0.557 mmol, Example 406) in ethanol (20 mL) was treated with 2-iodopropane (473 mg, 2.78 mmol) and K2CO3 (231 mg, 1.67 mmol) and was heated at reflux overnight. The reaction mixture was cooled and concentrated. The residue was diluted with H2O and ethyl acetate. The layers were separated, and the aqueous layer was extracted with ethyl acetate (2×). The combined organic layers were dried (MgSO4), filtered, and concentrated to yield an oil. Purification using silica gel chromatography (3:1 hexane:ethyl acetate) yielded 3-(2-(isopropoxycarbonylamino-methyl)-4-{2-[2-(4-isopropoxy-phenyl)-5-methyl-oxazol-4-yl]-ethoxy}-phenyl)-propionic acid tert-butyl ester as a yellow oil (210 mg). 1H NMR (300 MHz CDCl3) δ 1.28 (d, 6H), 1.40 (d, 6H), 1.45 (s, 9H), 2.38 (s, 3H), 2.53 (t, 2H), 2.91 (t, 2H), 2.99 (t, 2H), 4.25 (t, 2H), 4.39 (d, 2H), 4.66 (m, 1H), 5.00 (br m, 2H), 6.80 (dd, 1H), 6.87 (d, 1H), 6.95 (d, 2H), 7.13 (d, 1H), 7.95 (d, 2H) MS [ES] 581 (M+H).

Provenance & Evidence