Sodium hydride → HCID 15614947, compound

Participants

Reaction Conditions

Reaction Steps

Sodium hydride (80% by weight dispersion in mineral oil, 0.346 g, 1.1 eq) was added to a stirred solution of N-[[6-methoxy-2-(2,2,2-trifluoroethoxy)-5-(trifluoromethyl)-1-naphthalenyl]carbonyl]carbamic acid, ethyl ester (4.60 g, 10.5 mmol) in anhydrous tetrahydrofuran (125 mL) at room temperature under a dry nitrogen atmosphere. After 1 hour, the t-butyl bromoacetate (2.54 mL, 1.5 eq) was added. The reaction was heated to 65° C. for 1 hour, cooled to room temperature, and the THF was removed. The residue was dissolved in ether (200 mL), washed with water (2×50 mL) and saturated aqueous NaCl (1×50 mL). The ether phase was dried with magnesium sulfate and the ether was removed. The crude product was flash chromatographed (17:3 petroleum ether:ethyl acetate, silica) and triturated with petroleum ether to provide the title compound as a white powder (4.60 g, 79%), m.p. 84°-86° C.

Provenance & Evidence