Hydrochloric Acid → 3-[4-(2-{[(2,4-Difluoro-phenyl)-acetyl]-heptyl-amino}-ethyl)-phenyl]-2-ethoxy-propionic acid methyl ester

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Reaction Steps

To a solution of 2-ethoxy-3-[3-(2-heptylamino-ethyl)-phenyl]-propionic acid methyl ester HCl salt (43 mg, 0.11 mmol) and N,N-diisopropylethylamine (0.33 mmol, 0.058 mL) in anhydrous methylene chloride (2 mL) was added 2,4-difluorophenylacetyl chloride (0.128 mmol) in anhydrous methylene chloride (2 mL). The mixture was allowed to stir at room temperature for 16 hours. Then was poured over 1 M HCl (5 mL). The aqueous layer was isolated and extracted with methylene chloride (1×). The organic layers were combined, washed with 2 M HCl (1×), brine (1×), dried over anhydrous sodium sulfate, and concentrated to give a clear oil. The crude product was chromatographed on silica gel (Merck silica gel 60, art#9385-3) eluting with 20% ethyl acetate/hexanes to give 3-[4-(2-{[(2,4-difluoro-phenyl)-acetyl]-heptyl-amino}-ethyl)-phenyl]-2-ethoxy-propionic acid methyl ester as a clear oil (36.5 mg, 66%).

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