Dichloromethane → 256477-33-5

Participants

Reaction Steps

N-Berzylglycine t-butyl ester ##STR118## A solution of t-butyl bromoacetate (1.5 mL, 10.1 mmol) in CH2Cl2 (10 mL) was added dropwise to a stirred solution of benzylamine (10.9 mL, 100 mmol) in CH2Cl2 (40 mL) at 0° C., the mixture was stirred for 1 h and then warmed to room temperature and stirred for an additional 3 d. The mixture was washed with water (3×50 mL), dilute HCl (1 N) and the combined aqueous washings were extracted with Et2O. The organic phase was washed with saturated aqueous NaHCO3, dried (Na2SO4) and evaporated in vacuo. The residue was dissolved in Et2O, treated with a solution of HCl in ether (0.5 M) and the resulting precipitate was collected and dissolved in EtOAc. This solution was filtered through hyflo, and partially evaporated in vacuo to give a thick slurry. The solid was collected by filtration, washed with Et2O and then dried to give N-benzylglycine t-butyl ester hydrochloride (1.03 g, 4.00 mmol) as a white solid.

Provenance & Evidence