Water → Trifluoroacetic acid

Participants

Reaction Conditions

Reaction Steps

A mixture of ethyl 2-amino-2-methyl-4-(3-(5-phenyl-4-(trifluoromethyl)isoxazol-3-yl)-4,5-dihydronaphtho[1,2-c]isoxazol-7-yl)butanoate (Preparation 94A, isomer 1, 8 mg, 0.015 mmol), 2 M aqueous solution of sodium hydroxide (0.015 mL, 0.030 mmol), water (0.1 mL) and methanol (0.2 mL) was stirred at 66° C. under nitrogen for 30 min. Purification using reverse phase HPLC (Phenomenex Luna AXIA 5 u c18 30×100 mm, 10 min. run, solvent A: 10% MeOH: 90% H2O: 0.1% TFA, solvent B: 90% MeOH, 10% H2O, 0.1% TFA), concentration and lyophilization gave 2-amino-2-methyl-4-(3-(5-phenyl-4-(trifluoromethyl)isoxazol-3-yl)-4,5-dihydronaphtho[1,2-c]isoxazol-7-yl)butanoic acid, TFA (6 mg, 9.42 μmol, 61.9% yield) as a white solid. The compound had an HPLC retention time=3.45 min. (condition C); LC/MS M+1=498.5.

Provenance & Evidence