Methyl 6-chloro-6-oxohexanoate → Tert-butyl 2-{4-[(6-methoxy-6-oxohexanoyl)amino]benzoyl)hydrazinecarboxylate

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Reaction Steps

To a solution of tert-butyl 2-(4-aminobenzoyl)hydrazinecarboxylate (1.0 g, 3.98 mmol) in anhydrous pyridine (20 mL) was added dropwise methyl 6-chloro-6-oxohexanoate (Aldrich) (660 μL, 4.78 mmol) at rt. After 90 min, aminomethyl resin (Polymers Laboratories PL-AMS, 1.96 mmol/g, 960 mg) was added and the resulting mixture was stirred for 20 hrs at rt. After filtration and rinsing the resin, water (200 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 3 hrs. The title compound (1.27 g) was obtained as a white solid (80%) in 95.1% purity by HPLC (MaxPlot detection between 230 and 400 nm).

Provenance & Evidence