title: A modified, high yield procedure for the synthesis of unlabeled and 14C-labeled 4-methylene-DL-glutamic acid.
abstract: This paper describes the complete chemical synthesis of 4-methylene-DL-glutamic acid from diethylmalonate, formaldehyde and diethyl acetamidomalonate. The amino acid was obtained pure following ion-exchange chromatography and/or crystallization from hot water in an overall yield of 30% based on the amount of diethylmalonate used. Several physico-chemical characteristics of the synthetic compound were determined, including ir and pmr spectra, chromatography on paper, retention time on an amino acid analyzer, pK values and melting point; all properties of the synthetic material were found to be identical to those seen with the naturally occurring L-isomer. The procedure for obtaining gram quantities of the unlabeled compound has also been modified for the synthesis of high specific activity (10.6 mCi/mol) 4-methylene-[2-14C]-DL-glutamic acid.
mesh_terms: D002852:Chromatography, Ion Exchange; D003460:Crystallization; D004578:Electron Spin Resonance Spectroscopy; D005557:Formaldehyde; D005971:Glutamates / Q000138:chemical synthesis*; D008314:Malonates; D013055:Spectrophotometry, Infrared
chemical_list: D005971:Glutamates; D008314:Malonates; C030979:diethyl acetamidomalonic acid; D005557:Formaldehyde; C030977:4-methyleneglutamic acid; C030978:diethylmalonic acid