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Studies on the syntheses of analgesics. Part 50 . Synthesis of optically active 2‐[4‐(1‐oxo‐2‐isoindolinyl)phenyl]propanoic acid. [Studies on the syntheses of heterocyclic compounds. Part 742 ]
Author(s) -
Kametani Tetsuji,
Kigasawa Kazuo,
Hiiragi Mineharu,
Ishimaru Haruhide,
Haga Seiji,
Shirayama Keiko
Publication year - 1978
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570150304
Subject(s) - propanoic acid , chemistry , cinchonidine , reagent , resolution (logic) , stereochemistry , optically active , organic chemistry , combinatorial chemistry , enantioselective synthesis , catalysis , artificial intelligence , computer science
Abstract 2‐[4‐(1‐Oxo‐2‐isoindolinyl)phenyl]propanoic acid ( 1 ) having a potent analgesic and anti‐inflammatory activity could be obtained by three methods, which were found to provide extremely useful ways for the synthesis of 1 from the industrial point of view. (E)‐ and (Z)‐Isomers of 2‐butenoic acid and oxiranecarboxylic acid derivatives as the intermedaites in the synthesis of 1 were separated and characterized. Furthermore, the optical resolution of (±)‐2‐[4‐(1‐oxo‐2‐isoindolinyl)phenyl]propanoic acid was successfully achieved using cinchonidine as a resolution reagent.