HCID 14621631, compound → HCID 14621620, compound

Participants

Reaction Steps

A solution of N-benzoyl-N-[[6-methoxy-5-(trifluoromethyl)-1-naphthalenyl]carbonyl]glycine, 1,1-dimethylethyl ester (6.03 g, 12.4 mmole) in trifluoroacetic acid (40 mL) was stirred at room temperature for 10 minutes, then diluted with water (600 mL) and extracted with ether (2×300 mL). The extracts were combined, washed with saturated aqueous sodium chloride (1×100 mL), dried with magnesium sulfate, and the ether was removed. The resultant oil was suspended in water (300 mL) and the aqueous phase was slowly neutralized to pH 5 with 10% aqueous sodium hydroxide solution. The precipitate was collected by suction filtration, washed with water (2×25 mL), dried and flash chromatographed (9:1 chloroform:acetonitrile, 5% phosphoric acid in methanol treated silica). The solid was then recrystallized in 2:1 benzen:hexane to provide the product as white crystals (1.83 g, 33%), m.p. 143°-145° C. (dec.).

Provenance & Evidence