3-hydroxy-1,2,3-benzotriazin-4(3H)-one → [4-(3-Pyridyloxymethyl)-2-phenylbenzoyl]alanine methyl ester

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Reaction Steps

To a solution of 100 mg (0.33 mmol) of 4-(3-pyridyloxymethyl)-2-phenylbenzoic acid, L-alanine methyl ester hydrochloride (1.5 mmol), 69 mg (0.36 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, and 59 mg (0.36 mmol) of 3-hydroxy1,2,3-benzotriazin-4(3H)-one in 1 mL of N,N-dimethylformamide was added 5 drops of triethylamine. The mixture was stirred at ambient temperature for 24 hours, then poured into 10 mL of 0.6M aqueous sodium bicarbonate and extracted with ethyl acetate (3×5 mL). The combined ethyl acetate layers were back extracted with water (2×5 mL), then brine (1×5 mL), dried over magnesium sulfate, filtered, and concentrated in vacuo. The product was purified via chromatography over silica gel, eluting with an appropriate mixture of hexanes and ethyl acetate.

Provenance & Evidence