Hydrochloric Acid → 2-{4-[(tert-Butoxycarbonyl-methyl-amino)-methyl]-phenoxy}-2-methyl-propionic acid ethyl ester

Participants

Reaction Conditions

Reaction Steps

To an ice-cooled and stirred solution of 4.0 g (12 mmol) of the above prepared 2-[4-(tert-butoxycarbonylamino-methyl)-phenoxy]-2-methyl-propionic acid ethyl ester in 37 ml DMF was cooled (0° C.), and treated with 0.78 g (55% in oil, 18 mmol) of sodium hydride and, after 30 min, with 5.93 ml (95 mmol) of CH3I. The reaction was stirred at 0° C. to room temperature for 16 h. Subsequently, the solution was poured onto ice water, adjusted to pH 1 (with aqueous 1N HCl) and extracted with ether (two times). The organic layers were washed with water, dried (MgSO4), evaporated and purified by flash chromatography (SiO2, heptane/AcOEt=9:1) to finally give 3.68 g of the title compound as colorless oil.

Provenance & Evidence