Trifluoroacetic acid → Methyl [2-methyl-4-(methylamino)phenoxy]acetate

Participants

Reaction Steps

A solution of crude [4-(tert-butoxycarbonyl-methyl-amino)-2-methyl-phenoxy]-acetic acid methyl ester (25.8 g, 77 mmol) in CH2Cl2 (600 ml) was treated at 0° C. with TFA (198 ml) and stirred at RT for 30 min. The reaction was evaporated, treated with chilled aqueous saturated NaHCO3 solution/Et2O (3×). The organic phases were washed with aqueous 10% NaCl, dried (Na2SO4) and evaporated to give 16.2 g of crude (2-methyl-4-methylamino-phenoxy)-acetic acid methyl ester. Purification by flash chromatography with a gradient of n-heptane:EtOAc 9:1 to 4:1 yielded 12.7 g of (2-methyl-4-methylamino-phenoxy)-acetic acid methyl ester as an orange oil, MS: 210 (MH+).

Provenance & Evidence