Triethylamine → HCID 11638662, compound

Participants

Reaction Steps

400 mg (1.96 mmol) of para-tert.-butyl-trans-cinnamic acid were dissolved at 5° C. in DMF (10 ml) together with 290 mg (1.94 mmol) of 4-hydroxy-3-methoxybenzyl-amine hydrochloride and 0.48 ml (6.50 mmol) of triethylamine. After the addition of a solution of 870 mg (1.97 mmol) of BOP in DCM (9 ml), stirring was continued for 16 h at RT. The reaction solution was then poured into water and extracted twice with a mixture of DIPE/EA (1:1). The combined organic phases were washed with 2M eq. hydrochloric acid and three times with 1 M eq. of sodium hydrogen carbonate solution and dried over magnesium sulfate. Follwing removal of the solvents and recrystallisation from DIPE, 384 mg (1.13 mmol, 58% of theoretical) of para-tert.-butyl-trans-N-(4-hydroxy-3-methoxybenzyl)-cinnamic acid amide were obtained.

Provenance & Evidence