Cyclooctylamine → HCID 53872165, compound

Participants

Reaction Conditions

Reaction Steps

6.4 g (0.02 mol) of N-benzyloxycarbonyl-L-alanyl-L-proline were dissolved in 75 ml of dry tetrahydrofuran and the solution was cooled to -10° C. 2.54 ml (0.02 mol) of N-ethylmorpholine and 2.62 ml (0.02 mol) of isobutyl chloroformate were added and the resulting solution was stirred at -10° C. for 20 minutes. A solution of 2.5 g (0.02 mol) of cyclooctylamine in 25 ml of dry tetrahydrofuran was then added. The resulting mixture was stirred at 0° C. for 1 hour and then left to stand at room temperature for 16 hours. The tetrahydrofuran was removed by evaporation and the residue extracted with two 50 ml portions of ethyl acetate. The combined ethyl acetate extracts were washed successively with 1-N hydrochloric acid, water, 5% sodium bicarbonate solution and water and then dried over magnesium sulphate. Evaporation yielded an oil which solidified upon trituration with ether/petroleum ether. After recrystallisation from ethyl acetate/petroleum ether, there were obtained 5.1 g (59.3%) of N-benzyloxycarbonyl-L-alanyl-L-proline cyclooctylamide of melting point 94°-96° C.; [α]D20 =-95.0° (c=1.02% in methanol).

Provenance & Evidence