Carbon Tetrachloride → N,N'-di-(2-methylphenethyl)-2-((S)-2-mercapto-3-phenylpropionylamino)malonamide

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Reaction Steps

Combine of N,N′-di-(2-methylphenethyl)-2-((S)-2-(p-methoxybenzylmercapto)-3-phenylpropionylamino)malonamide (0.175 g, 0.274 mmol), mercury (II) acetate (0.108 g, 0.34 mmol), and anisole (0.3 mL) in dichloromethane (10 mL). Cool in an ice bath and degas by repeatedly applying vacuum and filling the vessel with nitrogen. Add trifluoroacetic acid (4 mL). After 3 hours, purge with hydrogen sulfide (gas) for about 10 minutes. Filter and evaporate in vacuo to give a residue. Combine the residue with carbon tetrachloride and evaporate in vacuo to remove most of the trifluoroacetic acid. Chromatograph the residue on silica gel eluting with 1/2 ethyl acetate/hexane and then 1/1 ethyl acetate/hexane to give the title compound.

Provenance & Evidence