Lithium Hydroxide → HCID 69744939, compound

Participants

Reaction Steps

A solution of 2-[[3-(2-amino-1,2-dioxoethyl)-2-methyl-1-(3-fluorobenzyl)-1,6,7,8-tetrahydrocyclopent[g]indol-4-yl]oxy]acetic acid methyl ester (500 mg, 1.14 mmol) in tetrahydrofuran (20 mL) and methanol (20 mL) was treated with 1 M aqueous lithium hydroxide (25 mL) at room temperature for 18 h. The resulting suspension was concentrated in vacuo and the residue diluted with water and adjusted to pH 2 with concentrated hydrochloric acid. After stirring for 1 h, the resulting precipitate was collected via vacuum filtration to provide 390 mg (77%) of the title compound as a solid. Recrystallization (methanol/water) of the residue provided an analytical sample as a yellow-green fibrous solid: mp 250-252° C. 1H NMR (DMSO-d6) δ 12.87 (bs, 1H), 7.71 (s, 1H), 7.42 (s, 1H), 7.37 (m, 1H), 7.10 (dt, J=10.6, 2.2 Hz, 1H), 6.77 (d, J=9.9 Hz, 1H), 6.69 (d, J=7.7 Hz, 1H), 6.47 (s, 1H), 5.56 (s, 2H), 4.62 (s, 2H), 2.93 (t, J=7.0 Hz, 2H), 2.82 (t, J=7.0 Hz, 2H), 2.41 (s, 3H), 1.97 (quintet, J=7.3 Hz, 2H); MS ES− m/e 423 (p−1); IR (KBr, cm−1) 3438, 1617, 1376.

Provenance & Evidence