Triethylamine → Carbamic acid, N-[3-[[2-(3-methoxyphenyl)ethyl]amino]-3-oxopropyl]-, 1,1-dimethylethyl ester

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Reaction Steps

3-methoxyphenethylamine (Aldrich, 100 mg, 0.66 mmol), 3-((tert-butoxycarbonyl)amino)-propanoic acid (125 mg, 0.66 mmol), hydroxybenzotriazole (8.9 mg, 0.066 mmol), triethylamine (102 μL, 0.73 mmol) and dimethyformamide (6.6 mL) were combined, then 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (139 mg, 0.73 mmol) was added. The solution was allowed to stir at room temperature overnight. Upon completion, ethyl acetate and water were added and the layers were separated. The aqueous phase was extracted with ethyl acetate then the combined organic layers were washed with brine and dried over Na2SO4. Solvent was removed under reduced pressure to give crude product which was purified by flash chromatography using 0-80% ethyl acetate/hexane as the eluent to give the product as a pure white solid (140 mg, 66%).

Provenance & Evidence