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

Participants

Reaction Steps

To an ice-cooled and stirred solution of 22.8 g (77 mmol) of the above prepared (4-tert-butoxycarbonylamino-2-methyl-phenoxy)-acetic acid methyl ester in 230 ml DMF was added within 10 min 3.7 g (55% in oil, 85 mmol) of NaH and, after 1 h, 14.5 ml (232 mmol) of CH3I. 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 over sodium sulfate, and evaporated to give 25.8 g of [4-(tert-butoxycarbonyl-methyl-amino)-2-methyl-phenoxy]-acetic acid methyl ester.

Provenance & Evidence