Tetrahydrofuran → 5-Tert-butyl-3-methanesulfonylamino-2-methoxy-benzoic acid methyl ester

Participants

Reaction Steps

To a 0° C. solution of 1.34 g (4.92 mmol) of N-(3-amino-5-tert-butyl-2-methoxy-phenyl)-methanesulfonamide and 1.3 mL (10 mmol) of 48% aqueous HBF4 in 10 mL of THF was added 586 mg (5 mmol) of isoamyl nitrite. The mixture was stirred 2 h, then the solvent was removed and the resulting orange semi-solid triturated with MTBE (3×10 mL). The resulting residue was taken up in MeOH and while CO was bubbled through, 60 mg of Pd(OAc)2 was added, and the mixture was stirred with continuous CO bubbling for 1 h. The solution was filtered, concentrated, and purified by chromatography (0 to 50% EtOAc in hexanes) to provide the title compound as a white solid (752 mg).

Provenance & Evidence