《AMG 837: A potent, orally bioavailable GPR40 agonist》 was published in Bioorganic & Medicinal Chemistry Letters in 2012. These research results belong to Houze, Jonathan B.; Zhu, Liusheng; Sun, Ying; Akerman, Michelle; Qiu, Wei; Zhang, Alex J.; Sharma, Rajiv; Schmitt, Michael; Wang, Yingcai; Liu, Jiwen; Liu, Jinqian; Medina, Julio C.; Reagan, Jeff D.; Luo, Jian; Tonn, George; Zhang, Jane; Lu, Jenny Ying-Lin; Chen, Michael; Lopez, Edwin; Nguyen, Kathy; Yang, Li; Tang, Liang; Tian, Hui; Shuttleworth, Steven J.; Lin, Daniel C.-H.. Application In Synthesis of (S)-3-(4-Hydroxyphenyl)hex-4-ynoic acid The article mentions the following:
The discovery that certain long chain fatty acids potentiate glucose stimulated insulin secretion through the previously orphan receptor GPR40 sparked interest in GPR40 agonists as potential antidiabetic agents. Optimization of a series of β-substituted phenylpropanoic acids led to the identification of (S)-3-(4-((4′-(trifluoromethyl)biphenyl-3-yl)methoxy)phenyl)hex-4-ynoic acid (AMG 837) as a potent GPR40 agonist with a superior pharmacokinetic profile and robust glucose-dependent stimulation of insulin secretion in rodents. The experimental part of the paper was very detailed, including the reaction process of (S)-3-(4-Hydroxyphenyl)hex-4-ynoic acid(cas: 865233-35-8Application In Synthesis of (S)-3-(4-Hydroxyphenyl)hex-4-ynoic acid)
(S)-3-(4-Hydroxyphenyl)hex-4-ynoic acid(cas: 865233-35-8) belongs to alkynes. The addition of nonpolar E−H bonds across C≡C is general for silanes, boranes, and related hydrides. The hydroboration of alkynes gives vinylic boranes which oxidize to the corresponding aldehyde or ketone. In the thiol-yne reaction the substrate is a thiol.Application In Synthesis of (S)-3-(4-Hydroxyphenyl)hex-4-ynoic acid
Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts