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

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Reaction Steps

1-Hydroxybenzotriazole (5.05 g, 1.5 eq) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (5.74 g, 1.2 eq) were added to a stirred solution of 6-methoxy-2-(2,2,2-trifluoroethoxy)-5-(trifluoromethyl)naphthoic acid, prepared by the process of Example 14 (9.18 g, 24.9 mmol) in anhydrous DMF (90 mL) at room temperature under a dry nitrogen atmosphere. After 11/4 hours, a suspension of methyl sarcosinate hydrochloride (6.96 g, 2.0 eq) in anhydrous DMF (40 mL) was added to the reaction followed by triethylamine (11.12 mL, 3.2 eq). After 30 minutes, the reaction was diluted with water (1.5 L) and extracted with ether (3×250 mL). The extracts were combined, dried with magnesium sulfate, and the ether was removed. The crude product was flash chromatographed (13:7→1:1 petroleum ether:ethyl acetate, silica) to provide the product as a clear oil (9.15 g, 81%). A small sample was triturated in petroleum ether to provide a white solid for analysis, m.p. 91.5°-93° C.

Provenance & Evidence