Beta-Alanine → HCID 66822401, compound

Participants

Reaction Steps

β-Alanine (71.3 mg, 0.8 mmol) and 1H-imidazole-2-carbaldehyde (19.2 mg, 0.2 mmol) were added successively to a stirred solution of 2-cyano-N-(1-(4-(methoxymethoxy)phenyl)butyl)acetamide (5; 27.6 mg, 0.1 mmol) in ethanol/water (2.0 mL/0.8 mL) at room temp. After 72 hours TLC (in 50% EtOAc/Hexane) showed a single product formed. The mixture was partitioned between aqueous sodium bicarbonate and ethyl acetate. The separated organic layer was washed with sat. brine and dried with sodium sulfate and concentrated to give a light amber oil (55 mg) as crude product. The crude material was purified by column chromatography to afford the titled compound as a yellow oil (23 mg) in 65% yield. 1H NMR (500 MHz, CDCl3) δ 10.59 (s, 1H), 8.14 (s, 1H), 7.42 (s, 1H), 7.23 (s, 1H), 7.17-7.13 (m, 2H), 7.12-7.07 (m, 2H), 5.22 (s, 2H), 3.86-3.75 (m, 2H), 3.51 (s, 3H), 1.64-1.53 (m, 2H), 1.36 (m, 2H), 0.93 (t, J=7.3, 3H). Mass spec ES+, m/z=355.1 (m+H+).

Provenance & Evidence