3-Fluorophenylacetic acid → HCID 67574108, compound

Participants

Reaction Steps

To a solution of 3-fluorophenylacetic acid (1.93 g, 12.5 mmol) in CH2Cl2 (50 mL) was added tert-butyl-N-(2-aminoethyl)carbamate (2.0 g, 12.5 mmol), 4-dimethylaminopyridine (1.53 g, 12.5 mmol) and 1-[3-dimethylamino)propyl]-3-ethyl carbodiimide hydrochloride (2.4 g, 12.5 mmol). The mixture was stirred at room temperature for 16 h then washed with water (50 mL) and citric acid (10%, 2×50 mL). The organic layer was separated, dried (Na2SO4) and evaporated. The residue was chromatographed on silica gel, eluting with CH2Cl2 :MeOH (95:5→90:10), to afford the title amide (3.7 g, 100%) as a colourless solid. mp 125-128° C. 1H NMR (250 MHz, CDCl3) δ 1.43 (9H, s), 3.18-3.40 (4H, m), 3.53 (2H, s), 4.82 (1H, br s), 6.23 (1H, br s), 6.94-7.06 (3H, m), 7.26-7.40 (2H, m). MS (ES+) (297, M+1).

Provenance & Evidence