Methyl iodide → [4-(Tert-butoxycarbonyl-methyl-amino)-2-methyl-phenoxy]-acetic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

To an ice-cooled and stirred solution of (4-tert-butoxycarbonylamino-2-methyl-phenoxy)-acetic acid methyl ester (22.8 g, 77 mmol) in DMF (230 ml) was added within 10 min NaH (3.7 g, 55% in oil, 85 mmol) and after 1 h, CH3I (14.5 ml, 232 mmol). The reaction was stirred at 0° C. for 2 h, neutralized with aqueous 10% KHSO4 and extracted with aqueous 10% KHSO4/Et2O (3×). The organic phases were washed with aqueous 10% NaCl, dried (Na2SO4) and evaporated to give 25.8 g of [4-(tert-butoxycarbonyl-methyl-amino)-2-methyl-phenoxy]-acetic acid methyl ester, MS: 310 (MH+).

Provenance & Evidence