Aniline → HCID 22843586, compound

Participants

Reaction Conditions

Reaction Steps

11.15 g (0.05 mol) of N-benzyloxycarbonyl-L-alanine were dissolved in 75 ml of dry tetrahydrofuran and the mixture was cooled to -10° C. 6.35 ml (0.05 mol) of N-ethylmorpholine were added followed by 6.5 ml of isobutyl chloroformate and the resulting solution was stirred at -10° C. for 20 minutes. 4.65 ml (0.05 mol) of aniline were then added, the mixture was stirred at 0° C. for 1 hour and then left to stand at room temperature for 3 hours. The solvents were removed by evaporation and the residue was dissolved in 200 ml of chloroform. The solution was washed with 150 ml of 1-N hydrochloric acid, 150 ml of water and 150 ml of 5% sodium bicarbonate solution, dried over magnesium sulphate and evaporated to give a white solid. This solid was treated with 300 ml of petroleum ether to yield 11.89 g (80%) of N-benzyloxycarbonyl-L-alanine anilide of melting point 161°-163° C.

Provenance & Evidence