Triethylamine → 2-(4-((((Tert-butoxy)carbonyl)amino)methyl)phenyl)acetic acid

Participants

Reaction Steps

A mixture of 7.76 g (38.5 mmol) of 4-aminomethylphenylacetic acid hydrochloride, 10.42 g (42.3 mmol) of 2-t-butoxycarbonyloxyimino-2-phenylacetonitrile and 13.33 ml (96.2 mmol) of triethylamine in 60 ml of 50% aqueous dioxane was stirred for 2.5 hours at ambient temperature. The solvent was removed, 25 ml of water and 50 ml of ethyl acetate were added and the layers were separated. The aqueous phase was extracted with ethyl acetate then stirred with ethyl acetate and acidified to pH 1-1.5 with 3 N hydrochloric acid. The mixture was then extracted three times with ethyl acetate and the combined extracts were washed with water, dried (MgSO4) and evaporated to give 4-(N-t-butoxycarbonylaminomethyl)phenylacetic acid, m.p. 108°-110°.

Provenance & Evidence