94429-35-3Relevant academic research and scientific papers
An efficient large-scale synthesis of a naphthylacetic acid CRTH2 receptor antagonist
Shu, Lianhe,Wang, Ping,Gu, Chen,Liu, Wen,Alabanza, Lady Mae,Zhang, Yingchao
, p. 651 - 657 (2013/06/27)
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.
