Benzyl-2-[2-(tert-butoxycarbonyl)-acetamido]acetate → 2-[2-(tert-Butoxycarbonyl)-acetamido]-acetic acid

Participants

Reaction Steps

Benzyl-2-[2-(tert-butoxycarbonyl)-acetamido]-acetate (14; 0.57 g, 1.85 mmol) was dissolved in methanol (15 mL), and then 10% Pd/C (0.06 g) was added therein with stirring for 1 h under pressure of 40 psi of hydrogen. After the reaction is completed, Pd/C was removed by filter paper and methanol was removed by concentration under reduced pressure to obtain colorless oil-like 15a (0.38 g; 100%). 1H-NMR (200 MHz) (DMSO) δ: 12.60 (br, s, 1H, CO2H), 8.07 (t, 1H, CONHCH2), 7.00 (t, 1H, NHBOC), 3.77 (d, 2H, CH2CO2H), 3.57 (d, 2H, CH2NHBOC), 1.40 [s, 9H, CO2C(CH3)3].

Provenance & Evidence