Glycine, N-[(2-chlorophenyl)methyl]-, methyl ester synthesis

Yield:133486-56-3 15.3 g (71%)

Reaction Conditions:

with triethylamine in N-methyl-acetamide;hexane;ethyl acetate;

Steps:

1.i (i)

(i) 5-Carboxymethyl-1-(2-chlorophenyl)methyl-2-thio-1H-imidazole A solution of 2-chlorobenzylamine (14.2 g, 0.1 mol) and triethylamine (13.9 mL, 0.1 mol) in dimethylformamide (100 mL) was treated with methyl chloroacetate (10.9 g, 0.1 mol). The mixture was heated at 50° C. for 3.5 hours. The cooled reaction mixture was diluted with diethyl ether, the solids filtered and the concentrated filtrate was flash chromatographed over silica gel with 6:4 hexane in ethyl acetate to provide 15.3 g (71%) of homogenous methyl 2-[N-(2-chloro-phenyl)methyl]aminoacetate.

References:

US2001/18448,2001,A1