Ethylmorpholine → HCID 53880215, compound

Participants

Reaction Conditions

Reaction Steps

3.2 g (0.01 mol) of N-benzyloxycarbonyl-L-alanyl-L-proline were dissolved in 50 ml of dry tetrahydrofuran and the solution was cooled to -10° C. 1.27 ml (0.01 mol) of N-ethylmorpholine were added followed by 1.31 ml (0.01 mol) of isobutyl chloroformate and the solution was stirred at -10° C. for 20 minutes. 1.21 ml (0.01 mol) of cyclohexylamine were then added and the mixture was stirred at 0° C. for 1 hour and then left to stand at room temperature for 16 hours. The mixture was evaporated and the residue was treated with 100 ml of ethyl acetate, washed with 80 ml of 1-N hydrochloric acid, 80 ml of water and 80 ml of 5% sodium bicarbonate solution, dried over sodium sulphate and evaporated to an oil. The product crystallised from ethyl acetate/ethyl to yield 2.36 g of N-benzyloxycarbonyl-L-alanyl-L-proline cyclohexylamide of melting point 130.5°-131.5° C. A second crop (0.95 g; melting point 130.5°-131.5° C.) was obtained on leaving the mother liquor to stand overnight. The total yield was 83%, [α]D20 =-96.3° (c=1.175% in methanol).

Provenance & Evidence