Sodium Hydroxide → HCID 39382716, compound

Participants

Reaction Steps

To a solution of methyl N-(tert-butoxycarbonyl)-N-(4-fluorobenzyl)glycinate (12.4 g, 41.6 mmol) in MeOH (180 mL) was added 5 N aqueous NaOH solution (18.3 mL, 91.6 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, washing 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 combined organic layers were dried (MgSO4) and concentrated in vacuo to afford the title acid as a light yellow oil. 1H NMR (400 MHz, CDCl3) δ 7.26-7.23 (m, 2H), 7.03 (br s, 2H), 4.50 (d, J=13.6 Hz, 2H), 3.96 (br s, 1H), 3.83 (br s, 1H), 1.49 (s, 9H). ES MS (M+1)=284.20

Provenance & Evidence