Triethylamine → N-[2-(Benzyloxy)benzoyl]-L-serine benzyl ester

Participants

Reaction Steps

To a stirred solution of 2-(benzyloxy)benzoic acid (2.0 g, 8.7 mmol), L-serine benzyl ester hydrochloride (2.0 g, 8.7 mmol, 1 equiv.) and HOAt (1.2 g, 8.7 mmol, 1 equiv.) in DMF (200 mL) was added triethylamine (0.98 mL, 9.6 mmol, 1.1 equiv.) and EDC HCl (2.02 g, 4.8 mmol, 1.2 equiv.). After being stirred overnight at room temperature under nitrogen, the reaction mixture was diluted with ethyl acetate (200 mL), washed with 1N HCl (60 mL), saturated NaHCO3, saturated NH4Cl (60 mL), and brine (60 mL). The combined organic layers were dried over Na2SO4, filtered, concentrated and chromatographed on silica gel eluting with CH2Cl2/MeOH (95/5) to give the title compound, N-[2-(benzyloxy)benzoyl]-L-serine benzyl ester, 92.5 g, 70%) as white crystals. Rf=0.5 (CH2Cl2/MeOH, 95/5); 1H NMR (300 MHz, CDCl3) δ8.80 (d, 1H, NH), 8.19 (dd,1H, ArH), 7.46-7.24 (m, 11H, ArH), 7.12-7.04 (m, 2H, ArH), 5.21-5.11 (m, 4H, 2{CH2phenyl}), 4.91-4.87 (m, 1H, CH), 3.93-3.90 (m, 2H, CH2OH), 2.2 (1H, OH).

Provenance & Evidence