Ethylamine → (S)-2-(Cbz-amino)-N-ethylpropanamide

Participants

Reaction Conditions

Reaction Steps

14 ml. of N-ethyl piperidine was added to a solution of 23.3 grams of benzyloxycarbonyl alanine in 100 ml. of tetrahydrofuran and, after cooling to -10 degrees C., 14 ml. of sec. butyl chlorformate was added. Next, the mixture was stirred for 8 minutes and cooled to -6 degrees C. Then 30 ml. of a 4.1 solution of ethylamine in tetrahydrofuran was added. After 30 minutes of stirring at 0 degrees C. and 2 hours of stirring at room temperature, the reaction solution was evaporated, gradually shaken with a 5% solution of sodium hydrogen carbonate, with water, dried with anhydrous sodium carbonate, and evaporated. The evaporation residue was crystallized from ethyl acetate (30 ml.) and petroleum ether. 18.1 g of a product having a melting point of 116 to 117 degrees C. was obtained.

Provenance & Evidence