Hydrochloric Acid → ethyl 2-amino-2-methyl-4-(3-(1-phenyl-5-(trifluoromethyl)-1H-pyrazol-4-yl)-4,5-dihydronaphtho[1,2-c]isoxazol-7-yl)butanoate

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Reaction Steps

To a stirred clear solution of ethyl 2-(diphenylmethyleneamino)-2-methyl-4-(3-(1-phenyl-5-(trifluoromethyl)-1H-pyrazol-4-yl)-4,5-dihydronaphtho[1,2-c]isoxazol-7-yl)butanoate (Preparation 50C, 120 mg, 0.174 mmol) in diethyl ether (3 mL) was added 4 N aqueous HCl (0.261 mL, 1.045 mmol) dropwise at room temperature. The reaction mixture was stirred at room temperature for 30 min. The ether layer was separated and the aqueous layer re-extracted with ether (2 mL). The aqueous solutions were basified with solid potassium carbonate and extracted with ethyl acetate (3×2 mL). The combined ethyl acetate extracts were dried over sodium sulfate and concentrated under reduced pressure to give ethyl 2-amino-2-methyl-4-(3-(1-phenyl-5-(trifluoromethyl)-1H-pyrazol-4-yl)-4,5-dihydronaphtho[1,2-c]isoxazol-7-yl)butanoate (86 mg, 0.164 mmol, 94% yield) as an yellow oil. The compound had an HPLC retention time=3.22 min (condition C); LC/MS M+1=525.5.

Provenance & Evidence