Methyl iodide → 4-(tert-Butoxycarbonyl-methyl-amino)-2-(3-methoxy-propyl)-phenoxy-acetic acid ethyl ester

Participants

Reaction Steps

To 2.21 g (6.01 mmol) of the above prepared [4-tert-butoxycarbonylamino-2-(3-methoxy-propyl)-phenoxy]-acetic acid ethyl ester, dissolved in 18 ml of abs. DMF, was added at 0° C. 0.313 g of NaH (60% in mineral oil, 1.3 eq.). 5 min later, 0.75 ml (2 eq.) of MeI was added and the reaction allowed to proceed for 10 min at 0° C. and for 1 h at ambient temperature. Pouring onto crashed ice/aqueous 10% KHSO4, twofold extraction with EtOAc, washing with water and brine, drying over magnesium sulfate, and evaporation of the solvents, followed by flash chromatography (SiO2, hexane/EtOAc=8/2), yielded 1.55 g of the title compound as light yellow oil.

Provenance & Evidence