Methyl iodide → HCID 69220575, compound

Participants

Reaction Steps

To an ice-cooled and stirred solution of (4-tert-butoxycarbonylamino-2-methyl-phenoxy)-acetic acid ethyl ester (3.09, 10 mmol) in DMF (30 ml) was added within 10 min NaH (55% in oil, 0.65 g, 15 mmol) and after 1 h, CH3I (4.98 ml, 80 mmol). The reaction was warmed up over night to RT, neutralized at 0° C. 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 3.46 g (quantitative) of [4-(tert-butoxycarbonyl-methyl-amino)-2-methyl-phenoxy]-acetic acid ethyl ester containing ca 20% (1H-NMR) of [4-(tert-butoxycarbonyl-methyl-amino)-2-methyl-phenoxy]-acetic acid methyl ester, MS: 323 (M, ethyl ester) and 309 (M, methyl ester).

Provenance & Evidence