Acetone → (4R)-4-((tert-Butoxycarbonyl)amino)-5-(4-(trifluoromethyl)phenyl)pentanoic acid

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Reaction Steps

(R)-tert-Butyl 2-(4-(trifluoromethyl)benzyl)-5-oxopyrrolidine-1-carboxylate (4.0 g, 12 mmol) was dissolved in 25 mL acetone and 40 mL of 1.0 M aqueous sodium hydroxide. The resulting mixture was stirred for 30 minutes. The acetone was removed and the mixture was acidified with 5.0 M HCl. The resulting solid was filtered and washed with water twice. The crude product was recrystallized from hexane/EtOAc solvent (10:1 ratio, total volume hexane: 100 mL). After the solution was cooled, the crystals slowly appeared and the solution was put in the freezer for 2 hours. Filtration of the solid afforded the desired compound as a white crystalline solid (3.9 g, 93%). MS (API-ES) m/z (%): 384.1 (100%, M++Na).

Provenance & Evidence