Synthesis of amino acid derivatives of ethanolamine

Summary N-Phthaloylglycylaminocthanol may be prepared in 24% yield by a modification of the Shechan carbodiimide synthesis of peptides of hydroxy amino acids (6). The amino alcohol is characterized as to melting point, solubility in various solvents, the ability to form a derivative with acetic anhydride, percentage of nitrogen, and infrared spectra. In acid solution this compound appears to undergo the aminoacyl shift characteristic of compounds containing an amide linkage and a free hydroxyl group. Attempts to isolated N-glycylaminoethanol by hydrolysis of the phthaloyl derivative with hydrazine hydrate have been unsuccessful. Impure N-phthaloylalanylaminoethanol and N-phthaloylglycylglycylaminoethanol were also synthesized by means of this procedure. Several other methods for synthesizing N-glycylaminoethanol are discussed. Portion of a thesis presented by Elizabeth C. Smith as partial fulfillment of the requirements for the degree of Doctor of Philosophy. Authorized for publication as Paper No. 2399 on Sept. 1, 1959, in the Journal Series of the Pennsylvania Agricultural Experiment Station.