FRINK Linked Data Fragments server

Matches in SemOpenAlex for { <https://semopenalex.org/work/W2012603417> ?p ?o ?g. }

• W2012603417 endingPage "440" @default.
• W2012603417 startingPage "431" @default.
• W2012603417 abstract "The first kilogram-scale synthesis of the PPARα agonist LY518674 (1) is described. The de novo convergent synthetic approach involved coupling of two rapidly assembled components, triazolone formation via a novel acid-promoted cyclization reaction, and final step saponification, delivering the compound in 32.5% overall yield via eight total steps with a six-step longest linear sequence. A regioselective alkylation on the dianion of 4-hydroxyphenylbutyric acid allowed the direct preparation of one of the convergent coupling partners, carboxylic acid 12, and an unusual solvent effect enabled the installation of a urea group on a protected hydrazine, permitting the regiospecific preparation of the other coupling partner, semicarbazide mesylate 17. Sulfonic acids were found to effect the desired triazolone ring formation, affording 25 from the coupled precursor acyl semicarbazide 23. Following saponification of 25 to 1, a wide solubility differential between ethyl acetate extracts of 1 and solutions of 1 in anhydrous ethyl acetate was harnessed in the final crystallization step to deliver the final compound in high yield and purity. The novel acid-mediated triazolone formation was further evaluated on a range of additional substrates, showing the new methodology to be largely complementary to existing base-mediated triazolone syntheses." @default.
• W2012603417 created "2016-06-24" @default.
• W2012603417 creator A5015573556 @default.
• W2012603417 creator A5023590360 @default.
• W2012603417 creator A5024689827 @default.
• W2012603417 creator A5027480161 @default.
• W2012603417 creator A5032992427 @default.
• W2012603417 creator A5037856745 @default.
• W2012603417 creator A5039207905 @default.
• W2012603417 creator A5048355659 @default.
• W2012603417 creator A5049450196 @default.
• W2012603417 creator A5054645643 @default.
• W2012603417 creator A5063361991 @default.
• W2012603417 creator A5073401324 @default.
• W2012603417 creator A5082903814 @default.
• W2012603417 date "2007-04-06" @default.
• W2012603417 modified "2023-09-24" @default.
• W2012603417 title "A Convergent Kilogram-Scale Synthesis of the PPARα Agonist LY518674: Discovery of a Novel Acid-Mediated Triazolone Synthesis" @default.
• W2012603417 cites W1554911347 @default.
• W2012603417 cites W1972994894 @default.
• W2012603417 cites W1980784087 @default.
• W2012603417 cites W1988496165 @default.
• W2012603417 cites W2020304486 @default.
• W2012603417 cites W2020830419 @default.
• W2012603417 cites W2054851194 @default.
• W2012603417 cites W2106193331 @default.
• W2012603417 cites W2150557496 @default.
• W2012603417 cites W2280337432 @default.
• W2012603417 cites W2333416050 @default.
• W2012603417 cites W2950235755 @default.
• W2012603417 cites W2952235721 @default.
• W2012603417 cites W2953165957 @default.
• W2012603417 cites W776602602 @default.
• W2012603417 doi "https://doi.org/10.1021/op700040v" @default.
• W2012603417 hasPublicationYear "2007" @default.
• W2012603417 type Work @default.
• W2012603417 sameAs 2012603417 @default.
• W2012603417 citedByCount "6" @default.
• W2012603417 countsByYear W20126034172012 @default.
• W2012603417 countsByYear W20126034172016 @default.
• W2012603417 countsByYear W20126034172022 @default.
• W2012603417 crossrefType "journal-article" @default.
• W2012603417 hasAuthorship W2012603417A5015573556 @default.
• W2012603417 hasAuthorship W2012603417A5023590360 @default.
• W2012603417 hasAuthorship W2012603417A5024689827 @default.
• W2012603417 hasAuthorship W2012603417A5027480161 @default.
• W2012603417 hasAuthorship W2012603417A5032992427 @default.
• W2012603417 hasAuthorship W2012603417A5037856745 @default.
• W2012603417 hasAuthorship W2012603417A5039207905 @default.
• W2012603417 hasAuthorship W2012603417A5048355659 @default.
• W2012603417 hasAuthorship W2012603417A5049450196 @default.
• W2012603417 hasAuthorship W2012603417A5054645643 @default.
• W2012603417 hasAuthorship W2012603417A5063361991 @default.
• W2012603417 hasAuthorship W2012603417A5073401324 @default.
• W2012603417 hasAuthorship W2012603417A5082903814 @default.
• W2012603417 hasConcept C134121241 @default.
• W2012603417 hasConcept C155574463 @default.
• W2012603417 hasConcept C15761196 @default.
• W2012603417 hasConcept C161790260 @default.
• W2012603417 hasConcept C164361826 @default.
• W2012603417 hasConcept C178790620 @default.
• W2012603417 hasConcept C185592680 @default.
• W2012603417 hasConcept C191897082 @default.
• W2012603417 hasConcept C192562407 @default.
• W2012603417 hasConcept C21951064 @default.
• W2012603417 hasConcept C2778627024 @default.
• W2012603417 hasConcept C2780365088 @default.
• W2012603417 hasConcept C39409265 @default.
• W2012603417 hasConcept C59759590 @default.
• W2012603417 hasConcept C60002323 @default.
• W2012603417 hasConceptScore W2012603417C134121241 @default.
• W2012603417 hasConceptScore W2012603417C155574463 @default.
• W2012603417 hasConceptScore W2012603417C15761196 @default.
• W2012603417 hasConceptScore W2012603417C161790260 @default.
• W2012603417 hasConceptScore W2012603417C164361826 @default.
• W2012603417 hasConceptScore W2012603417C178790620 @default.
• W2012603417 hasConceptScore W2012603417C185592680 @default.
• W2012603417 hasConceptScore W2012603417C191897082 @default.
• W2012603417 hasConceptScore W2012603417C192562407 @default.
• W2012603417 hasConceptScore W2012603417C21951064 @default.
• W2012603417 hasConceptScore W2012603417C2778627024 @default.
• W2012603417 hasConceptScore W2012603417C2780365088 @default.
• W2012603417 hasConceptScore W2012603417C39409265 @default.
• W2012603417 hasConceptScore W2012603417C59759590 @default.
• W2012603417 hasConceptScore W2012603417C60002323 @default.
• W2012603417 hasIssue "3" @default.
• W2012603417 hasLocation W20126034171 @default.
• W2012603417 hasOpenAccess W2012603417 @default.
• W2012603417 hasPrimaryLocation W20126034171 @default.
• W2012603417 hasRelatedWork W2001656747 @default.
• W2012603417 hasRelatedWork W2012603417 @default.
• W2012603417 hasRelatedWork W2019919093 @default.
• W2012603417 hasRelatedWork W2028445891 @default.
• W2012603417 hasRelatedWork W2047888616 @default.
• W2012603417 hasRelatedWork W2321123841 @default.
• W2012603417 hasRelatedWork W2343977437 @default.
• W2012603417 hasRelatedWork W2949821387 @default.
• W2012603417 hasRelatedWork W2950536755 @default.

• next