Benzyl Bromide → [(2-Benzyloxy-phenyl)-tert-butoxycarbonylmethyl-amino]-acetic acid tert-butyl ester

Participants

Reaction Conditions

Reaction Steps

A solution of [tert-Butoxycarbonylmethyl-(2-hydroxy-phenyl)-amino]-acetic acid tert-butyl ester (11) (7.4 g, 21.9 mmol) in dry THF (50 mL) was treated with sodium hydride (0.81 g, 33.8 mmol) at 0° C. under an Ar atmosphere. After stirring at 0° C. for 30 min, benzyl bromide (3.9 mL, 32.7 mmol) was added. The mixture was stirred at 0° C. for another 30 min and then warmed to room temperature overnight. The reaction mixture was quenched with H2O and extracted with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4 and concentrated in vacuo. The crude product was purified by flash column chromatography, eluting with CH2Cl2/hexane/EtOAc=1:4:0.2 to yield 6.3 g (67%) of the desired product 12 as a colorless oil. Rf=0.33 (in CH2Cl2/hexane/EtOAc=1:4:0.2); 1H NMR (300 MHz, CDCl3) δ 7.45-7.28 (m, 5H), 6.84 (m, 4H), 5.12 (s, 2H), 4.08 (s, 4H), 1.40 (s, 18H); 13C NMR (75 MHz, CDCl3) δ 170.5, 150.5, 139.6, 137.5, 128.4, 127.6, 127.2, 121.9, 121.4, 119.4, 114.7, 81.0, 70.9, 54.6, 28.0; mass spectrum, calculated for C25H33NO5 (MH+) 428.2, Found 427.9.

Provenance & Evidence