Sodium Hydroxide → HCID 27281430, compound

Participants

Reaction Steps

To a solution of methyl 3-(4-amino-1-naphthyl)-N-(tert-butoxycarbonyl)-L-alaninate (2.4 g, 7.0 mmol) in methanol (10 mL) was added 8M aqueous NaOH (1.5 mL, 12 mmol) and the mixture was stirred at ambient temperature for 45 minutes. The mixture was concentrated under reduced pressure, taken up in water (5 mL) and extracted with diethyl ether (2×10 mL). The aqueous layer was then shaken with ethyl acetate (30 mL) and 1M HCl (13 mL). The layers were separated, and the aqueous layer was extracted with ethyl acetate (1×20 mL). The combined ethyl acetate layers were washed with brine (1×5 mL), dried (MgSO4), filtered, and concentrated under reduced pressure to provide the titled compound (1.9 g, 83%).

Provenance & Evidence