Sodium Chloride → N,N'-di-(4-chlorophenethyl)-2-((S)-2-(p-methoxybenzylmercapto)-3-phenylpropionylamino)malonamide

Participants

Reaction Steps

Combine 2-((S)-2-(p-methoxybenzylmercapto)-3-phenylpropionylamino)malonic acid (prepared by the method of Preparation 5, 0.476 g, 63% acid/37% sodium chloride, 0.74 mmol), dichloromethane (9 mL), and tetrahydrofuran (1.5 mL). Add 4-chlorophenylethylamine (0.31 mL, 2.23 mmol), N-methylmorpholine (0.25 mL, 2.3 mmol), 1-ethyl-3-(3-(dimethylamino)propyl)carbodiimide hydrochloric acid salt (0.427 g, 2.23 mmol) and 1-hydroxybenztriazole hydrate (0.301 g, 2.23 mmol). After 3 days, concentrate in vacuo and partition the concentrated reaction mixture between an aqueous 5% sulfuric acid solution and ethyl acetate. Separate the layers and extract the organic layer with a saturated aqueous sodium bicarbonate solution and then brine. Dry the organic layer over Na2SO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting sequentially with 2/3 ethyl acetate/hexane, 1/1 ethyl acetate/hexane, and then 1/2 ethyl acetate/hexane to give the title compound.

Provenance & Evidence