1-Hydroxybenzotriazole → 4-[2-(N'-{3-[5-(4-Methoxy-phenyl)-oxazol-2-yl]-benzoyl}-hydrazino)-2-oxo-ethyl]-benzoic Acid Methyl Ester

Participants

Reaction Steps

0.7 g (2.0 mmol) of 3-[5-(4-Methoxy-phenyl)-oxazol-2-yl]-benzoic acid hydrazide hydrochloride from Preparation 6, 0.49 g (2.6 mmol) EDAC.HCl, 0.35 g (2.6 mmol) HOBT, and 0.50 g (2.6 mmol) 4-carboxymethyl-benzoic acid methyl ester from Preparation 7 was dissolved in 20 mL of dimethylformamide. 0.33 g (2.6 mmol) Di-isopropylethylamine was then added. Stirring was continued 14 hours at room temperature. Water (60 ml) was added and the product was extracted with 1:1 Et2O/EtOAc (2×). Combined the organic extracts and washed with saturated aqueous NaCl solution (4×), dried (MgSO4). The resulting solid was triturated in EtOAc and filtered. Dried in a vacuum oven overnight at 70° C. to provide 0.48 g (49%) desired product. MS: m/z (APCI, AP+) 486 [M−]+

Provenance & Evidence