Phenethylamine → HCID 18348138, compound

Participants

Reaction Steps

Combine a mixture of t-butoxycarbonylaminomalonic acid and sodium chloride from Preparation 1.2 (5.0 g, 13.7 mmol), phenethylamine (4.32 mL, 34.3 mmol), and tetrahydrofuran (25 mL). Cool in an ice bath. Remove the ice bath. Add N-methylmorpholine (3.8 mL, 34.3 mmol), 1-ethyl-3-(3-(dimethylamino)propyl)carbodiimide hydrochloric acid salt (6.58 g, 34.3 mmol), and 1-hydroxybenztriazole hydrate (4.63 g, 34.3 mmol). Allow to warm to ambient temperature. After 18 hours, dilute the reaction mixture with ethyl acetate, extract with an aqueous 5% sulfuric acid solution, a saturated sodium bicarbonate solution, and then brine. Dry the organic layers over Na2SO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting with 2/1 ethyl acetate/hexane to give the title compound (84%).

Provenance & Evidence