Lithium Hydroxide → HCID 10223013, compound

Participants

Reaction Steps

A solution of 2-[[3-(2-amino-1,2-dioxoethyl)-2-methyl-1-benzyl-1,6,7,8-tetrahydrocyclopent[g]indol-4-yl]oxy]acetic acid methyl ester (95 mg, 0.23 mmol) in a 1:1 mixture of methanol/tetrahydrofuran (1 mL) was treated with excess 1M lithium hydroxide for 19 h at room temperature. The mixture was concentrated in vacuo, diluted with water, and acidified with 5N hydrochloric acid. The resulting precipitate was collected via vacuum filtration and recrystallized (absolute ethanol) to provide 65 mg (71%) of the title product as yellow crystals: mp 255-257° C. 1H NMR (DMSO6) δ 12.84 (bs, 1H, —OH), 7.69 (bs, 1H), 7.33 (m, 4H), 6.92 (d, J=7.0 Hz, 2H), 6.46 (s, 1H), 5.54 (s, 2H), 4.61 (s, 2H), 2.95 (t, J=7.0 Hz, 2H), 2.82 (t, J=7.3 Hz, 2H), 2.42 (s, 3H), 1.96 (quintet, J=7.0 Hz, 2H); MS ES+ m/e 407 (p+1).

Provenance & Evidence