Triethylamine → Dibenzo[b,f]oxepine-10-carboxylic acid [(1S*,2S*,4R*)-1-(3-benzyloxy-benzyl)-4-butylcarbamoyl-2-hydroxy-pentyl]-amide

Participants

Reaction Steps

(1S*,2S*,4R*)-1-(3-Benzyloxy-benzyl)-4-butylcarbamoyl-2-hydroxy-pentyl-ammonium chloride (210 mg, 0.48 mmol), Dibenzo[b,f]oxepine-10-carboxylic acid (138 mg, 0.58 mmol, 1.2 eq), EDCl (139 mg, 0.72 mmol, 1.5 eq), HOBt (78 mg, 0.58 mmol, 1.2 eq) and triethylamine (0.20 ml, 1.4 mmol, 3 eq) are dissolved in DCM (12 ml) and stirred at rt for 3 days. EtOAc is added. After washing with 0.5 N HCl, brine, bicarbonate and brine again, drying over magnesium sulfate, the solvent is evaporated and the residue recrystallized from DCM/ether/hexane with a drop of methanol to give a white solid (240 mg).

Provenance & Evidence