Methanol → 3-Cyano-6-chloro-2-[3-(tert-butoxycarbonyl)amino-benzo[d]isoxazol-5-ylmethyl]aminocarbonylmethyl-pyridine 1-oxide

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Reaction Steps

A mixture of 6-chloro-3-cyano-2-(4-nitro-phenoxycarbonylmethyl)-pyridine 1-oxide (83.6 mg, 0.25 mmol), as prepared in Example 6f, and (5-aminomethyl-benzo[d]isoxazol-3-yl)-carbamic acid tert-butyl ester (78.8 mg, 0.3 mmol) in CDCl3 (3 mL) was stirred in an ice-water bath which was allowed to rise to rt overnight. A lot of precipitate formed. TLC showed the disappearance of 6-chloro-3-cyano-2-(4-nitro-phenoxycarbonylmethyl)-pyridine 1-oxide. A small amount of methanol was added to dissolve the solid. The solution was applied onto a prep TLC (2 mm, 20×20 cm) and developed with EtOAc/Hexane (4:1). A white solid was obtained (103 mg). LC/MS (ESI) (M+H+ 458.1)

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