Lithium Hydroxide → HCID 10113775, compound

Participants

Reaction Steps

A solution of 2-[[3-(2-amino-1,2-dioxoethyl)-1-benzyl-2-ethyl-6,7,8,9-tetrahydro-1H-benz[g]indol-4-yl]oxy]acetic acid methyl ester (150 mg, 0.334 mmol) in 3:1 tetrahydrofuran/methanol (4 mL) was treated with 1 M lithium hydroxide solution (1 mL) at room temperature for 1 h. The reaction mixture was concentrated in vacuo to one half the original volume and treated with 1 M hydrochloric acid (1 mL). The resulting suspension was diluted with water (5 mL), stirred, and the precipitate collected via vacuum filtration. This material was washed with water and dried to provide 128 mg (88%) of the title compound as a yellow solid: mp 222-225° C. 1H NMR (DMSO-d6) δ 7.72 (bs, 1H), 7.33 (m, 0.4H), 6.87 (d, J=7.3 Hz, 2H), 6.23 (s, 1H), 5.65 (s, 2H), 4.56 (s, 2H), 2.87 (m, 2H), 2.72 (m, 4H), 1.59 (m, 4H), 1.07 (t, J=7.3 Hz, 3H); MS ES+ m/e 435 (p+1); IR (CHCl3, cm−1) 3507, 3472, 3393, 2938, 1759, 1640.

Provenance & Evidence