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Synthesis of tritiated β‐(S‐benzylmercapto)‐β,β‐cyclopentamethylene propionic acid
Author(s) -
Landvatter Scott W.,
Heys J. Richard
Publication year - 1987
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.2580240611
Subject(s) - chemistry , tritium , cyclohexanone , hydrolysis , tritium illumination , tritiated water , catalysis , esterase , ring (chemistry) , organic chemistry , radiochemistry , enzyme , physics , nuclear physics
β‐(S‐benzylmercapto)‐β,β‐cyclopentamethylene propionic acid has been tritium labeled in the cyclohexyl ring. A key feature of the synthesis is the reduction of phenolwith tritium gas over catalyst giving tritiated cyclohexanone. A Wadsworth‐Emmons reaction followed by esterase hydrolysis of the resulting ester and Michael addition of p ‐methylbenzylmercaptan afford the title compound.