HCID 67457217, compound → 1-(4-(5-(5-Phenyl-4-(trifluoromethyl)isoxazol-3-yl)-1,2,4-oxadiazol-3-yl)benzyl)azetidine-3-carboxylic acid

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Reaction Steps

A solution of tert-butyl 1-(4-(5-(5-phenyl-4-(trifluoromethyl)isoxazol-3-yl)-1,2,4-oxadiazol-3-yl)benzyl)azetidine-3-carboxylate (293 mg, 0.556 mmol) in trifluoroacetic acid (4 mL) was allowed to stand at room temperature for 1.5 h. The volatiles were removed under reduced pressure, and the residue was suspended in water (5 ml). The pH was adjusted to −4 with a 1N aqueous solution of sodium hydroxide with stirring. The resulting thick suspension was stirred at room temperature for 1 hr. The precipitate was collected by vacuum filtration and dried well under reduced pressure. The compound was suspended in methanol and stirred at room temperature for 18 hr. The product was collected by vacuum filtration, washed with methanol, and dried well under reduced pressure to afford 1-(4-(5-(5-phenyl-4-(trifluoromethyl)isoxazol-3-yl)-1,2,4-oxadiazol-3-yl)benzyl)azetidine-3-carboxylic acid (194 mg, 0.412 mmol, 74.1% yield) as a white, crystalline solid.

Provenance & Evidence