Ammonium Chloride → 2-(Benzhydrylidene-amino)-3-(3-nitro-phenyl)-propionic acid ethyl ester

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Reaction Steps

To a solution of (benzhydrylidene-amino)-acetic acid ethyl ester (2.84 g, 10.4 mmol) in anhydrous tetrahydrofuran (15 mL) at −78° C. under an atmosphere of argon was added a 1 M solution of potassium tert-butoxide in tetrahydrofuran (11 mL, 11 mmol) to form a red/orange solution. After stirring at −78° C. for 15 minutes a solution of 1-bromomethyl-3-nitro-benzene (2.14 g, 9.7 mmol) in tetrahydrofuran (20 mL) was added and the reaction mixture left to warm slowly to ambient temperature and stir for 16 hours. To the reaction mixture was added saturated aqueous ammonium chloride (20 mL), the mixture was poured into water (100 mL), diluted with brine (50 mL) and extracted with ethyl acetate (3×50 mL). The combined organic extracts were washed with brine (2×50 mL), dried over sodium sulfate and concentrated in vacuo to give crude 2-(benzhydrylidene-amino)-3-(3-nitro-phenyl)-propionic acid ethyl ester as a red/brown viscous oil which was used without further purification (4.1 g, ≈100%).

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