Synthesis of a tetraamido macrocycle ligand

Details Synthesis of a tetraamido macrocycle ligand Synthesis of a tetraamido macrocycle ligand

1999-05-25

2000-10-03

Shah, Mukund J.

Organic compounds -- part of the class 532-570 series

Organic compounds

Unsubstituted hydrocarbyl chain between the ring and the -c-...

540461, 540452, 540465, C07D22500

Patent

active

061275360

ABSTRACT:
An improved synthesis for preparing a tetraamido-macrocyclic ligand, such as 5,6-Benzo-3,8,11,13-tetraoxo-2,2,9,9-tetramethyl-12,12-diethyl-1,4,7,10 -tetraazacyclotridecane, H.sub.4, in greatly improved yield and in a commercially viable manner, comprising the steps of dissolving a quantity of a 1,2-bis(2-aminoalkanamido)benzene in a solution comprised of ethyl acetate and methylene chloride to yield a first reaction solution; dissolving a quantity of a malonyl dihalide in an ethyl acetate solution to yield a second reaction solution; adding the first reaction solution and the second reaction solution to a reaction vessel containing a third reaction solution comprised of refluxing ethyl acetate solution and an acid scavenger to form a reaction mixture; and isolating a solid product comprised of the tetraamido-macrocycle directly from the reaction mixture by filtration.

REFERENCES:
patent: 5853428 (1998-12-01), Collins et al.
Bradshaw et al., Chap VIII in Aza-Crown Macrocycles., John Wiley & Sons 1993, p. 402.

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