27955-23-3Relevant academic research and scientific papers
A facile one-pot preparation of alkyl aminoaryl sulfides for the synthesis of GW7647 as an agonist of peroxisome proliferator-activated receptor α
Ham, Jungyeob,Cho, Sung Jin,Ko, Jaeyoung,Chin, Jungwook,Kang, Heonjoong
, p. 5781 - 5784 (2006)
We have developed two simple and high yielding one-pot syntheses of alkyl aminoaryl sulfides containing a series of four-steps: in situ protection of the free amine by reaction with a Grignard reagent, halogen-lithium exchange, sulfur insertion, and a substitution reaction with various electrophiles. Through this protocol, we have successfully synthesized tert-butyl-2-[4-(2-aminoethyl) phenylsulfanyl]-2-methylpropanoate, a key intermediate for the synthesis of GW7647 and GW9578 (ureido-TiBAs), in 92% yield. Furthermore, we were able to improve the overall yield of, GW7647 to 66%, 3 times the yield previously reported.
