Sodium Hydroxide → N-(tert-Butoxycarbonyl)-N-(4-fluorobenzyl)glycine

Participants

Reaction Steps

To a solution of methyl N-(tert-butoxycarbonyl)-N-(4-fluorobenzyl)glycinate (12.37 g, 41.63 mmol) in MeOH (180 mL) was added 5 N aqueous NaOH solution (18.32 mL, 91.58 mmol). The reaction was stirred under inert atmosphere at ambient temperature for 2 h. The solvent was removed in vacuo, and the remaining residue was taken up in water and washed twice with CHCl3. The aqueous layer was cooled to 0° C., acidified to pH 2 with 1 N aqueous HCl solution, and saturated with NaCl. The mixture was extracted with EtOAc three times, and the organic layers were dried (MgSO4) and concentrated in vacuo to afford the acid as a light yellow oil.

Provenance & Evidence