(4-Nitrophenyl)acetic acid → HCID 10248394, compound

Participants

Reaction Steps

ADL-01-0079-2 was prepared via the general EDCI/DIPEA coupling procedure from 28 (1.5 g; 7.3 mmol), 4-Nitrophenylacetic acid(2.0 g; 11.0 mmol), HOBT (1.4 g; 11 mmol), EDCI (2.1 g; 11.0mmol), and DIPEA (2.5 mL; 14.6 mmol). The crude product was purified by flash chromatography using a stepwise gradient of 1% to 5% MeOH: methylene chloride to afford 2.5 g(93%) of pure product which was treated with 1.0HCl in diethyl ether to give 39 as the HCl salt. 1H NMR(HCl salt, CDCl3) δ1.6(br, m, 4H, —CH2CH2—), 2.8(br, s, 3H, —NCH3), 6.4(br, m,1H, —CH), 7.1-7.5(complex, 7H, aromatic), 8.0(br, d, 2 h, aromatic). MS (FAB) m/z 367. Anal. (C,H,N) C21H25N3O3.HCl.

Provenance & Evidence