Hydrochloric Acid → (2S)-2-Amino-N,N-dimethyl-3-phenylpropanamide hydrochloride
Reaction equation
[CH3:1][N:2]([CH3:21])[C:3](=[O:20])[C@H:4]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[NH:5]C(OC(C)(C)C)=O.[ClH:22]>CO>[ClH:22].[NH2:5][C@@H:4]([CH2:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:3]([N:2]([CH3:21])[CH3:1])=[O:20]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
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 toluene (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).