ChemInform Abstract: ANTIINFLAMMATORY PHENYLACETIC ACID DERIVATIVES. III. 4‐CYCLOHEXYLPHENYLACETIC C ACID OXYGENATED DERIVATIVES

Maillard, J.; Langlois, Michel; Delaunay, Pierre; Tri, Vo Van Tri Vo Van; Meingan, J.-P.; Rapin, M; Morin, Richard P.; Manuel, C.; Mazmanian, C.

doi:10.1002/chin.197726211

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2013

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“…Though the Heck reaction of a close analogue of 17 is known in the literature, no reaction between 17 and 23 was detected under similar conditions (Scheme ). Friedel–Crafts reactions of analogues of 25 , an alternative approach, have also been reported . However, with compound 25 , the reactions were poor under all conditions examined (Scheme ).…”

Section: Resultsmentioning

confidence: 99%

An Efficient Large-Scale Synthesis of a Naphthylacetic Acid CRTH2 Receptor Antagonist

Shu

Wang

et al. 2013

Org. Process Res. Dev.

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An efficient and practical synthesis of a naphthylacetic acid CRTH2 receptor antagonist is reported. Michael addition of ethyl t-butyl malonate to an allenoate afforded a triester, which was selectively hydrolyzed and decarboxylated to give a benzylidenepentanedioic acid monoester. Treatment of this compound with potassium acetate and acetic anhydride produced the naphthylacetate core. The triflate of the key building block was coupled with a zinc reagent of the side chain under improved Negishi coupling conditions to afford the target product. The process was successfully scaled up to produce over 2 kg of the API.

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Section: Resultsmentioning

confidence: 99%