Antineoplastic agents. XIX. N-Bis(2-haloethyl)glycine amides | Zendy

George R. Pettit | Zendy; Maurice R. Chamberland | Zendy; Brian Green | Zendy

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Antineoplastic agents. XIX. N-Bis(2-haloethyl)glycine amides

Author(s) -

George R. Pettit,

Maurice R. Chamberland,

Brian Green

Publication year - 1967

Publication title -

canadian journal of chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.323

H-Index - 68

eISSN - 1480-3291

pISSN - 0008-4042

DOI - 10.1139/v67-252

Subject(s) - chemistry , amine gas treating , glycine , hydrochloride , medicinal chemistry , tetrahydrofuran , oxalyl chloride , bromide , chloride , derivative (finance) , organic chemistry , amino acid , biochemistry , solvent , financial economics , economics

A number of routes to N-bis(2-fluoroethyl)glycine (IIIa) were explored. Of these, condensation between N-bis(2-fluoroethyl)amine and bromoacetic acid in tetrahydrofuran proved to be the most satisfactory. Reaction between a carbonic anhydride derivative of, for example, glycine IIIa and the appropriate aromatic amine provided the glycine amides summarized by structures IVb-IVi. Treatment of N-bis(2-chloroethyl)glycine hydrochloride with oxalyl chloride at steam-bath temperature yielded N-bis(2-chloroethyl)amine hydrochloride as the major product.

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