Hydrogen Peroxide → (R)-methyl 5-(sec-butylamino)-4-(aminocarbonyl)-2-methylbenzoate

Participants

Reaction Steps

To a cooled (0° C.) solution of (R)-methyl 5-(sec-butylamino)-4-cyano-2-methylbenzoate (300 mg, 1.22 mmol) in DMSO (1.5 mL) was added 30% hydrogen peroxide solution (258 μL, 8.96 mmol) and potassium carbonate (56 mg, 0.402 mmol). The reaction mixture was allowed to warm to room temperature and stirred for 4 h, at which time it was concentrated in vacuo. The residue was purified by flash chromatography (100% hexanes to 10% ethyl acetate in hexanes) to afford (R)-methyl 5-(sec-butylamino)-4-(aminocarbonyl)-2-methylbenzoate (300 mg, 93%) as yellow crystals. MS (EI) for C14H20N2O3: 265 (MH+).

Provenance & Evidence