Lithium Hydroxide → HCID 11281695, compound

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Reaction Steps

A solution of 2-[[3-(2-amino-1,2-dioxoethyl)-2-methyl-1-(4-fluorobenzyl)-1,6,7,8-tetrahydrocyclopent[g]indol-4-yl]oxy]acetic acid methyl ester (0.34 g, 0.78 mmol) in tetrahydrofuran (15 mL) and methanol (15 mL) was treated with 1 M aqueous lithium hydroxide solution (20 mL) at room temperature for 66 h. The mixture was concentrated in vacuo and the residue acidified with concentrated hydrochloric acid. The resulting precipitate was collected via vacuum filtration, washed with water, and air-dried to provide 168 mg (51%) of the title compound as a green solid: mp 199-201° C. (dec). 1H NMR (DMSO-d6) δ 13.10 (bs, 1H), 7.18 (m, 2H), 6.95 (m, 2H), 6.50 (s, 1H), 5.55 (s, 2H), 4.62 (s, 2H), 2.95 (t, J=6.6 Hz, 2H), 2.83 (t, J=7.0 Hz, 2H), 2.50 (s, 3H), 1.98 (quintet, J=7.3 Hz, 2H).

Provenance & Evidence