Methyl chloroacetate → N-(3,5-difluorobenzyl)-glycine methyl ester

Participants

Reaction Steps

A solution of 3,5-difluorobenzylamine (12.3 g, 0.0863 mole), methyl chloroacetate (7.6 ml, 0.0863 mole) and triethylamine (12.0 ml, 0.0863 mole) in dry dimethylformamide (85 ml) was heated at 60° C. for 3 hours. The mixture was diluted with an equal volume of ether and the triethylamine hydrochloride filtered. The filtrate was concentrated under vacuum and the resultant oil triturated with ethyl acetate and the solution decanted from a small amount of residual oil. The solvent was removed and the product was purified by flash chromatography (silica) by eluting with hexane-ethyl acetate (70:30) to give an oil (7.61 g, 41%).

Provenance & Evidence