Process development of a large-scale synthesis of TKA731: A tachykinin receptor antagonist

…, A Chaudhary, O Repič, TJ Blacklock…

Index: Prashad, Mahavir; Har, Denis; Hu, Bin; Kim, Hong-Yong; Girgis, Michael J.; Chaudhary, Apurva; Repic, Oljan; Blacklock, Thomas J.; Marterer, Wolfgang Organic Process Research and Development, 2004 , vol. 8, # 3 p. 330 - 340

Full Text: HTML

Citation Number: 14

Abstract

An efficient and chromatography-free large-scale synthesis of a tachykinin receptor antagonist TKA731 (1), utilizing the coupling of dipeptide 7 and 2-chloro-4 (3H)- quinazolinone (13) as the key step, is described. The overall yield of 1 from BOC-l-3-(2- naphthyl) alanine (2) in six linear steps (total of eight steps) is 63%. This new convergent approach avoided the use of methyl iodide and the formation of methanethiol byproduct in ...