Triethylamine → N-cyanoacetyl-L-alanyl-L-proline anilide

Participants

Reaction Conditions

Reaction Steps

1.7 g (0.005 mol) of L-alanyl-L-proline anilide hydrobromide were dissolved in 50 ml of dichloromethane at 0° C. 0.42 g (0.005 mol) of cyanoacetic acid, 0.7 ml (0.005 mol) of triethylamine and 1.1 g of N,N-dicyclohexylcarbodiimide were added and the mixture was stirred at 0° C. overnight. The solvent was removed by evaporation, the residue suspended in 50 ml of ethyl acetate, the suspension filtered and the filtrate washed with 1-N hydrochloric acid, water, 5% sodium bicarbonate solution and water, dried over magnesium sulphate and evaporated to give a white solid. Recrystallisation of this solid from ethyl acetate yielded 0.6 g (37%) of N-cyanoacetyl-L-alanyl-L-proline anilide of melting point 183°-184° C.; [α]D20 =-204.6° (c=0.78% in methanol).

Provenance & Evidence