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 ] | Zendy

Kametani Tetsuji | Zendy; Kigasawa Kazuo | Zendy; Hiiragi Mineharu | Zendy; Ishimaru Haruhide | Zendy; Haga Seiji | Zendy; Shirayama Keiko | Zendy

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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

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.

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