Sodium hydride → (4-{Tert-butoxycarbonyl-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethyl]-amino}-phenoxy)-acetic acid ethyl ester

Participants

Reaction Steps

To an ice-cooled and stirred solution of (4-tert-butoxycarbonylamino-phenoxy)-acetic acid ethyl ester (0.295, 1 mmol) and 5-chloromethyl-2-(4-trifluoromethyl-phenyl)-thiazole (0.292, 1 mmol) in DMA (10 ml) was added NaH (55% in oil, 0.065 g, 1.5 mmol). The reaction was warmed up and stirred for 5 h at 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. Purification by flash chromatography with a gradient of CH2Cl2:Et2O 99:1 to 98:2 yielded 0.207 g (38%) of (4-{tert-butoxycarbonyl-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethyl]-amino}-phenoxy)-acetic acid ethyl ester as a yellow viscous oil, MS: 551 (MH+).

Provenance & Evidence