Butanoic acid, 4-chloro-4-oxo-, methyl ester → Tert-butyl 2-{4-[(4-methoxy-4-oxobutanoyl)amino]benzoyl}hydrazinecarboxylate

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Reaction Steps

To a solution of tert-butyl 2-(4-aminobenzoyl)hydrazinecarboxylate (500 mg, 1.99 mmol) in anhydrous pyridine (10 mL) was added dropwise 3-carbomethoxypropionyl chloride (Fluka) (300 μL) at rt. After 60 min, aminomethyl resin (Polymers Laboratories PL-AMS, 1.96 mmol/g, 400 mg) was added and the resulting mixture was stirred overnight at rt. After filtration and rinsing the resin, water (80 mL) was added into the filtrate and a white solid precipitated out. Filtration and washing with water gave a white solid, which was dried under vacuo at 70° C. for 2 hrs. The title compound (461 mg) was obtained as a white solid (63%) in 96.0% purity by HPLC (MaxPlot detection between 230 and 400 nm).

Provenance & Evidence