Lithium Hydroxide → 5-Cyano-2-[3-methyl-2,5-dioxo-1-(3-trifluoromethyl-phenyl)-1,2,3,4,5,6,7,8-octahydro-quinazolin-4-yl]-benzoic acid

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Reaction Steps

5-Cyano-2-[3-methyl-2,5-dioxo-1-(3-trifluoromethyl-phenyl)-1,2,3,4,5,6,7,8-octahydro-quinazolin-4-yl]-benzoic acid methyl ester (INTERMEDIATE 24, 5.3 g, 11 mmol) and lithium hydroxide (0.78 g, 32.9 mmol) are stirred in 1.4-dioxane (90 ml) and water (30.0 mL) at room temperature for 7.5 h. The reaction mixture is diluted with water and the extracted with diethyl ether. The aqueous phase is acidified with hydrochloric acid to a pH of 2 and extracted with ethyl acetate. The ethyl acetate phase is evaporated under reduced pressure and the crude product is purified by reversed phase HPLC. Yield: 1.5 g; ESI mass spectrum [M+H]+=470; Retention time HPLC: 0.61 min (X012_S02).

Provenance & Evidence