Direct synthesis of 1,1'-[1,4-phenylenebis(methylene)]-bis- 1,4,8,11-tetraazacyclotetradecane octahydrochloride (AMD 3100) without the use of protecting groups.
A four-step synthesis of the title compound starting from methyl acrylate, ethylenediamine, and dimethyl malonate is reported. The synthesis can be run on a multigram scale and is operationally simple. The use of protecting groups is avoided by utilizing the trioxocyclam as the key coupling intermediate.
Achmatowicz
Michal
M
Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523, USA. hegedus@lamar.colostate.edu
Hegedus
Louis S
LS
D000179:Acrylates; D019380:Anti-HIV Agents / Q000138:chemical synthesis*; D001596:Benzylamines; D000080027:Cyclams; D005029:Ethylenediamines / Q000737:chemistry; D006571:Heterocyclic Compounds / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy
D000179:Acrylates; D019380:Anti-HIV Agents; D001596:Benzylamines; D000080027:Cyclams; D005029:Ethylenediamines; D006571:Heterocyclic Compounds; D007202:Indicators and Reagents; C031234:ethylenediamine; C088327:plerixafor; C035956:methyl acrylate