APC-2848, K02

Chemical Name: N-(4-Morpholinylcarbonyl)-L-phenylalanine 1(S)-(2-phenylethyl)-3-(phenylsulfonyl)-2(E)-propenyl amide
CAS No. 170111-23-6
项目整合开发状态: Preclinical
项目研究机构: Celera (Originator), Khepri (Originator), Aventis Pharma (Codevelopment)
合成路线:N-Boc-Homophenylalanine (I) was coupled to N,O-dimethyl hydroxylamine using DCC,and the resulting N-methoxy amide (II) was reduced to aldehyde (III) with LiAlH4.Sulfonyl phosphonate (VI),(prepared from methyl phenyl sulfone (IV) and diethyl chlorophosphate (V)),was then condensed with aldehyde (III) in the presence of NaH to provide the vinylogous sulfone (VII).Subsequent acid deprotection of the Boc group of (VII) yielded amine (VIII).This was finally coupled with mixed anhydride (X),(obtained from morpholinocarbonyl-phenylalanine (IX) and isobutyl chloroformate in the presence of N-methylmorpholine),to furnish the target amide.