Dimethylamine → (S)-2-amino-3-(4-chloro-phenyl)-N,N-dimethyl-propionamide trifluoroacetate salt

Participants

Reaction Conditions

Reaction Steps

A mixture of Boc-L-4-chlorophenylalanine (Bachem California Inc., Torrance, Calif., USA; 5.0 g, 16.7 mmol), dimethylamine (2 M in tetrahydrofuran; 12.5 mL, 25 mmol), 1-hydroxybenzotriazole (available from 3B Scientific Corporation, Libertyville, Ill. 60048, USA; 2.69 g, 19.9 mmol), O-benzotriazol-1-yl-N,N,N′,N′-tetramethyluronium hexafluororophosphate (available from Aldrich Chemical Company, Inc., 1001 West Saint Paul Avenue, Milwaukee, Wis. 53233, USA; 7.5 g, 19.8 mmol) and diisopropylethylamine (8.8 mL, 50.5 mmol) in N,N-dimethylformamide was stirred at 0° C. for 30 min and then at room temperature for 10 min. Ethyl acetate was added and the mixture was washed with water and brine. The organic phase was dried over sodium sulfate, filtered and evaporated to give a white solid. The solid was dissolved in dichloromethane (30 mL). Trifluoroacetic acid (30 mL) was added and the solution was stirred for 2 h at room temperature. The solvents were evaporated to give (S)-2-amino-3-(4-chloro-phenyl)-N,N-dimethyl-propionamide trifluoroacetate salt as a white solid.

Provenance & Evidence