BIO-5192

(2S)-2-[[[((2S)-1-[(3,5-二氯苯基)磺酰基]-2-吡咯烷基]羰基]氨基]-4-[[(2S)-4-甲基-2-[甲基[2-[4-[[[[((((2-(甲基苯基)氨基)羰基]氨基]苯基]乙酰基]氨基]-1-氧戊基]氨基]丁酸)Chemical Name: 2(S)-[1-(3,5-Dichlorophenylsulfonyl)-L-prolylamino]-4-[N-methyl-N-[2-[4-[3-(2-methylphenyl)ureido]phenyl]acetyl]-L-leucylamino]butyric acid
CAS No. 327613-57-0
项目整合开发状态: Preclinical
项目研究机构: Biogen Idec (Originator)
合成路线:2-N-(Benzyloxycarbonyl)-L-2,4-diaminobutyric acid (I) is esterified by means of SOCl2 in MeOH to afford the corresponding methyl ester (II).Subsequent coupling of (II) with N-Boc-N-methyl-L-leucine (III) leads to dipeptide (IV).The N-benzyloxycarbonyl group of (IV) is removed by catalytic hydrogenation over Pd/C to furnish amine (V),which is further acylated with N-benzyloxycarbonyl-L-proline succinimidyl ester (VI) yielding tripeptide (VII).Then,acidic cleavage of the N-Boc protecting group (VII) produces (VIII).

合成路线:Coupling of p-aminophenylacetic acid (IX) with o-tolyl isocyanate (X) produces urea (XI).This is subsequently condensed with the intermediate tripeptide (VIII) in the presence of HATU to yield amide (XII).Hydrogenolysis of the N-benzyloxycarbonyl group of (XII) then gives amine (XIII).Finally,acylation of amine (XIII) with 3,5-dichlorobenzensulfonyl chloride (XIV),followed by alkaline hydrolysis of the methyl ester group furnishes the title compound.