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General procedure: Lauric acid (12.0 g, 60 mmol) dissolved in dry ethyl acetate (100 mL) was added to a solution of N-hydroxysuccinimide (NHS) (6.9 g, 60 mmol) and N,N?-dicyclohexylcarbodiimide (DCC) (12.4 g, 60 mmol) in dry ethyl acetate (300 mL). The reaction mixture was left overnight at room temperature. Dicyclohexylurea (DCU) was removed by filtration and the filtrate was evaporated under reduced pressure to yield white crystals (17.4 g, 95 percent yield). Recrystallization from ethanol yielded 16.6g of pure dodecanoic acid 2,5-dioxo-pyrrolidine-1-yl ester. Tyrosine ethyl ester hydrochloride (TEEH) (12.6 g, 51 mmol) was dissolved in dry chloroform (300 mL) and neutralized by addition of triethylamine (TEA) (10 mL). To this solution was added dry dodecanoic acid 2,5-dioxo-pyrrolidine-1-yl ester (15.2 g, 51 mmol) and the reaction mixture was stirred for 24 h at room temperature. Solvent was evaporated under reduced pressure. Residue was dissolved in methylene chloride (300 mL) and the solution was washed with aqueous citric acid solution. Organic solvent layer was separated, dried over MgSO4 and then evaporated to dryness to obtain the white crystalline solid, the tyrosine-lauramide conjugate (Tyr-Lau), which was further purified by silica column chromatography (EtOAc/n-Hexane 2:3). Yield: 96 percent.
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