Sodium Hydroxide → HCID 10344629, compound

Participants

Reaction Steps

A solution of the ethyl ester from example 47 (100 mg, 0.20 mmol) and 2N sodium hydroxide solution (2 ml) in dioxan (4 ml) was stirred at 50° C. for 3 hours, then concentrated under reduced pressure. The residue was suspended in 2N hydrochloric acid (2 ml), extracted with ethyl acetate (3×20 ml), and the combined organic solutions dried (MgSO4) and evaporated under reduced pressure. The crude product was purified by column chromatography on silica gel using an elution gradient of ethyl acetate:methanol:acetic acid (90:10:0 to 90:10:1) to afford the title compound as a colourless oil, 50 mg; 1H NMR (CDCl3, 400 MHz) δ: 1.45–1.78 (m, 8H), 1.85–2.19 (m, 6H), 2.56 (m, 1H), 2.62 (m, 2H), 3.37 (m, 4H), 3.46 (m, 1H), 4.00 (t, 2H), 4.62 (m, 1H), 6.64 (d, 1H), 6.81 (d, 2H), 7.22 (d, 2H); LRMS: m/z (ES−) 468 [M-H]−.

Provenance & Evidence