BCH-2687, LEF-553

Chemical Name: L-Tyrosyl-D-arginyl-L-phenylalanyl-L-phenylalaninamide
CAS No. 171807-58-2
项目整合开发状态: Phase II
项目研究机构: AstraZeneca (Originator)
合成路线:Fmoc-protected phenylalanine (I) is attached to Rink resin by means of DCC and HOBt coupling,to give the amino acid-resin complex (II).Then,N-Fmoc protecting group is removed with piperidine in DMF to afford (III).This is submitted to further sequential amino acid coupling and deprotection cycles with Fmoc-phenylalanine (I) and alpha-Fmoc-omega-pmc-D-arginine (VI) to yield in turn resins (V) and (VII),respectively.

合成路线:Compound (VII) is submitted to amino acid coupling and deprotection cycle with O-t-Bu-alpha-Fmoc-tyrosine (IX),to yield resin (XI).Finally,acidic treatment of (XI) with trifluoroacetic acid in anisole and dichloromethane simultaneously effects deprotection of the O-tert-butyl and N-2,2,5,7,8-pentamethylchroman-6-sulfonyl (Pmc) groups,and liberates the peptide amide from the resin.