Hydrochloric Acid → (2S)-2-Amino-N,N-dimethyl-3-phenylpropanamide hydrochloride

Participants

Reaction Steps

To a solution of N-tert-butyloxycarbonyl-(S)-phenylalanine dimethylamide (Preparation 7, 24.8 g, 84 mmol) in methanol (50 mL) was added a solution of hydrochloric acid (4N, in dioxane, 40 mL) and the mixture stirred at rt for 3 h. The resulting solution was concentrated in vacuo then dissolved in water (300 mL). The aqueous solution was washed with ethyl acetate (3×100 mL) and concentrated again. Successive recrystallisations with methanol (200 mL) and a mixture of methanol and (1:1, 200 mL) gave the title compound as colourless crystals. δH (D2O) 2.75, 2.90 (6H, 2×s), 3.18 (2H, m), 4.72 (1H, t), 7.28-7.45 (5H, m).

Provenance & Evidence