Hydrochloric Acid → 8-[5-(Trifluoromethyl)-5-(3,5-dichlorophenyl)-2-isoxazoline-3-yl]indolizine-5-carboxylic acid

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Reaction Steps

A solution of ethyl 8-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)indolizine-5-carboxylate (50 mg, 0.11 mmol) and NaOH (21 mg, 0.55 mmol) in H2O-MeOH (1:1, 20 mL) was stirred at rt for 3 h. The mixture was acidified with 2 N HCl and extracted with ethyl acetate (3×20 mL). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by prep-TLC to give 8-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)indolizine-5-carboxylic acid (23 mg, yield 47%) as a yellow solid. MS: m/z=443.7 (M+1, ESI+).

Provenance & Evidence