L-685458

(5S)-(叔丁氧羰基氨基)-6-苯基-(4R)-羟基-(2R)-苄基己酰)-L-亮氨酰-L-苯丙氨酰胺Chemical Name: N-[2(R)-Benzyl-5(S)-(tert-butoxycarboxamido)-4(R)-hydroxy-6-phenylhexanoyl]-L-leucyl-L-phenylalanylamide
CAS No. 292632-98-5
项目整合开发状态: Preclinical
项目研究机构: Merck Sharp & Dohme (Originator)
合成路线:The alkylation of N-[1(S)-(5-oxotetrahydrofuran-2(R)-yl)-2-phenylethyl]carbamic acid tert-butyl ester (I) with benzaldehyde (II) by means of LDA in THF,followed by a treatment with Ac2O and TEA at 120 C,gives the benzylidene derivative (III),which is hydrogenated with H2 over Pd/C in methanol/ethyl acetate to yield N-[1(S)-[4(R)-benzyl-5-oxotetrahydrofuran-2(R)-yl]-2-phenylethyl]carbamic acid tert-butyl ester (IV).The hydrolysis of (IV) with NaOH in dimethoxyethane/water affords the hexanoic acid (V),which is finally condensed with the dipeptide L-leucyl-L-phenylalaninamide (VI) by means of EDC and HOBT in DMF to provide the target acylated dipeptide.