Hydrochloric Acid → Ethyl 2-amino-3-(3-nitrophenyl)propanoate

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Reaction Steps

To a solution of crude 2-(benzhydrylidene-amino)-3-(3-nitro-phenyl)-propionic acid ethyl ester (4.1 g, ≈10.2 mmol) in ether (100 mL) was added 1M aqueous hydrochloric acid and the mixture stirred vigorously at ambient temperature for 4 hours. The layers were separated and the organic layer extracted with 1M aqueous hydrochloric acid (3×50 mL). The combined aqueous layers were cautiously adjusted to pH=8 with solid potassium carbonate and then extracted with ethyl acetate (3×100 mL). The combined organic extracts were washed with brine (150 mL), dried over sodium sulfate and concentrated in vacuo to give crude 2-amino-3-(3-nitro-phenyl)-propionic acid ethyl ester. The crude amine was dissolved in acetonitrile (100 mL), di-tert-butyldicarbonate (2.4 g, mmol) added and the mixture stirred at ambient temperature for 16 hours. The reaction mixture was poured into water (500 mL), extracted with ether (3×100 mL), the combined organic extracts were washed with 0.1M aqueous hydrochloric acid (100 mL), saturated aqueous sodium bicarbonate (100 mL), brine (100 mL), dried over sodium sulfate and concentrated in vacuo to give crude 2-tert-butoxycarbonylamino-3-(3-nitro-phenyl)-propionic acid ethyl ester as an orange/yellow viscous oil (3.35 g, ≈97%).

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