Hydrochloric Acid → HCID 9959108, compound

Participants

Reaction Steps

To 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 (83 mg, 0.20 mmol) in methylene chloride (3 mL) was added diisopropylethylamine (0.1 mL, 0.6 mmol), 4-N,N-dimethylaminopyridine (24 mg, 0.20 mmol), benzenesulfonamide (31 mg, 0.20 mmol), and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (58 mg, 0.37 mmol). The mixture was stirred at room temperature for 18 h. Additional portions of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (29 mg), diisopropylethylamine (51 μL), and benzenesulfonamide (16 mg) were added and the resulting mixture stirred for 5 h. The mixture was poured into 1 N hydrochloric acid and extracted three times with methylene chloride. The combined methylene chloride extracts were washed once with water, once with saturated aqueous sodium chloride solution, dried (sodium sulfate), filtered, and concentrated in vacuo. Chromatography (silica gel, 7% methanol/93% chloroform) of the residue provided a solid that was slurried in hot ethyl acetate. Collection of the resulting solid via vacuum filtration provided 10 mg (9%) of the title compound as a yellow solid. 1H NMR (CDCl3) δ 10.95 (s, 1H), 7.91 (d, J=7.7 Hz, 2H), 7.55 (t, J=7.4 Hz, 1H), 7.38 (t, J=7.7 Hz, 2H), 7.20-7.35 (m, 4H), 6.91 (d, J=7.0 Hz, 2H), 6.21 (s, 1H), 5.84 (bs, 1H), 5.48 (s, 2H), 4.55 (s, 2H), 2.98 (t, J=7.3 Hz, 2H), 2.71 (t, J=7.7 Hz, 2H), 2.48 (s, 3H), 2.01 (quintet, J=7.7 Hz, 2H).

Provenance & Evidence