Triethylamine → HCID 15614966, compound

Participants

Reaction Steps

1-Hydroxybenzotriazole hydrate (2.45 g, 1.5 eq) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (2.78 g, 1.2 eq) was added to a stirred solution of 2-chloro-6-methoxy-5-(trifluoromethyl)naphthoic acid (3.69 g, 12.11 mmol, prepared by the process of Step 3, Example 12) in dry dimethylformamide (78 mL). After stirring 11/2 hours at room temperature, glycine t-butyl ester hydrochloride (4.06 g, 2 eq) and triethylamine (dried over KOH, 5.8 mL, 3.3 eq) were added. After stirring 3 hours the reaction mixture was diluted with water (1 L) and extracted with ether (3×350 mL). Silica gel was added to the extracts and the solvent was removed. The absorbate was flash chromatographed (70:30 petroleum ether:ethyl acetate) to give the title compound as a white solid (3.95 g, 80%), m.p. 166°-167° C.

Provenance & Evidence