(2S,3S)-N-[(1S)-2-hydroxy-1-(1H-indol-3-ylmethyl)ethyl]-3-methyl-2-[(1-naphthylsulfonyl)amino]pentanamide -Drug Synthesis Database

【结构式】

【分子编号】18651

【品名】(2S,3S)-N-[(1S)-2-hydroxy-1-(1H-indol-3-ylmethyl)ethyl]-3-methyl-2-[(1-naphthylsulfonyl)amino]pentanamide

【CA登记号】

【分子式】C₂₇H₃₁N₃O₄S

【分子量】493.62696

【元素组成】C 65.7% H 6.33% N 8.51% O 12.96% S 6.5%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号：(VII)

Title compound was prepared by two related ways: N-(Benzyloxycarbonyl)-L-tryptofanol (I) was deprotected by hydrogenolysis in the presence of Pd/C. The resulting tryptofanol (II) was then coupled with N-(benzyloxycarbonyl)-L-isoleucine (III), using 1-(3-diethylaminopropyl)-3-ethylcarbodiimide.HCl (EDC) and 1-hydroxybenzotriazole (HOBt) to provide (IV). Subsequent hydrogenolytic deprotection gave amine (V), which was condensed with 1-naphthalenylsulfonyl chloride (VI) in the presence of 4-(dimethylamino)pyridine to afford sulfonamide (VII). Finally, oxidation with DMSO in the presence of SO3-pyridine complex yielded the aldehyde.

参考文献中间体

合成目标

【1】 Yasuma, T.; Oi, S.; Choh, N.; Nomura, T.; Furuyama, N.; Nishimura, A.; Fujisawa, Y.; Sohda, T.; Synthesis of peptide aldehyde derivatives as selective inhibitors of human cathepsin L and their inhibitory effect on bone resorption. J Med Chem 1998, 41, 22, 4301.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(I)	18645	benzyl (1S)-2-hydroxy-1-(1H-indol-3-ylmethyl)ethylcarbamate		C₁₉H₂₀N₂O₃	详情	详情
(II)	18646	(2S)-2-amino-3-(1H-indol-3-yl)-1-propanol		C₁₁H₁₄N₂O	详情	详情
(III)	23508	(2S,3S)-2-[[(benzyloxy)carbonyl]amino]-3-methylpentanoic acid	3160-59-6	C₁₄H₁₉NO₄	详情	详情
(IV)	18648	benzyl (1S,2S)-1-([[(1S)-2-hydroxy-1-(1H-indol-3-ylmethyl)ethyl]amino]carbonyl)-2-methylbutylcarbamate		C₂₅H₃₁N₃O₄	详情	详情
(V)	18649	(2S,3S)-2-amino-N-[(1S)-2-hydroxy-1-(1H-indol-3-ylmethyl)ethyl]-3-methylpentanamide		C₁₇H₂₅N₃O₂	详情	详情
(VI)	18650	1-naphthalenesulfonyl chloride	85-46-1	C₁₀H₇ClO₂S	详情	详情
(VII)	18651	(2S,3S)-N-[(1S)-2-hydroxy-1-(1H-indol-3-ylmethyl)ethyl]-3-methyl-2-[(1-naphthylsulfonyl)amino]pentanamide		C₂₇H₃₁N₃O₄S	详情	详情

Extended Information