Premium
Synthesis of carboxy‐polyethylene glycol‐amine (CA (PEG) n ) and [1‐ 14 C]‐CA (PEG) n via oxa‐Michael addition of amino‐polyethylene glycols to propiolates vs to acrylates
Author(s) -
Song Fengbin,
Chen Lu,
Lin Ronghui,
Salter Rhys
Publication year - 2020
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.3816
Subject(s) - polyethylene glycol , chemistry , synthon , peg ratio , amine gas treating , michael reaction , adduct , polyethylene , peg 400 , addition reaction , organic chemistry , polymer chemistry , combinatorial chemistry , catalysis , finance , economics
Synthesis of carboxy‐polyethylene glycol‐amine (CA (PEG) n ) via oxa‐Michael addition of amino‐polyethylene glycols to either acrylates or propiolates was investigated. Compared with the oxa‐Michael addition to acrylates, the corresponding addition to propiolates was found to proceed under mild reaction conditions and afford the adducts in high yields from a broad scope of substrates. A two‐step efficient and convenient synthesis of benzyl [1‐ 14 C]‐propiolate from 14 CO 2 was therefore developed and utilized as a common synthon to afford practical and high yielding access to [1‐ 14 C]‐CA (PEG) n .