1-Hydroxybenzotriazole → 2-hydroxy-8-phenyl-N-((5-phenyl-1,3,4-oxadiazol-2-yl)methyl)octanamide

Participants

Reaction Steps

To a solution of 2-hydroxy-8-phenyloctanoic acid (458 mg, 1.94 mmol), 5-phenyl-1,3,4-oxadiazol-2-yl methanamine oxalate (514 mg, 1.94 mmol), HOBt (314 mg, 2.3 mmol) and diisopropylethyl amine (501 mg, 3.9 mmol) in DMF (15 mL) was added 1-ethyl-3(3-dimethylaminopropyl) carbodiimide hydrochloride (446 mg, 2.3 mmol). The suspension was stirred for 48 h then filtered. The filtrate was diluted with EtOAc and washed sequentially with water, saturated NaHCO3, and brine. The organic phase was dried (Na2SO4) and filtered and the residue triturated with EtOAc to yield 2-hydroxy-8-phenyl-N-((5-phenyl-1,3,4-oxadiazol-2-yl)methyl)octanamide (MH+=394).

Provenance & Evidence