Triethylamine → N-[[6-Methoxy-2-(2,2,2-trifluoroethoxy)-5-(trifluoromethyl)-1-naphthalenyl]carbonyl]glycine, 1,1-Dimethylethyl Ester

Participants

Reaction Steps

1-Hydroxybenzotriazole (4.27 g, 1.5 eq) and 1-(3-dimethylaminopropyl)-3-ethoxycarbodiimide hydrochloride (4.84 g, 1.2 eq), were added to a stirred solution of 6-methoxy-2-(2,2,2-trifluoroethoxy)-5-(trifluoromethyl)naphthoic acid (7.75 g, 21.0 mmol, prepared by the process of Example 11, Step 3) in anhydrous dimethylformamide (135 mL) under a dry nitrogen atmosphere at room temperature. After 11/4 hours, glycine, t-butyl ester hydrochloride (7.06 g, 2.0 eq) and anhydrous triethylamine (9.68 mL, 3.3 eq) were added. After another 2 hours, the reaction mixture was diluted with water (1.5 L) and extracted with ether (4×200 mL). The extracts were combined and the ether was removed. The crude product was flash chromatographed (7:3 petroleum ether:ethyl acetate, silica) to provide the title compound as a white solid (7.39 g, 73%), m.p. 146°-174.5° C.

Provenance & Evidence