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【结 构 式】

【分子编号】58948

【品名】methyl (1R,2S)-1-{[((2S,4R)-1-{(2S)-2-[(tert-butoxycarbonyl)amino]-8-nonenoyl}-4-hydroxypyrrolidinyl)carbonyl]amino}-2-vinylcyclopropanecarboxylate

【CA登记号】

【 分 子 式 】C26H41N3O7

【 分 子 量 】507.62756

【元素组成】C 61.52% H 8.14% N 8.28% O 22.06%

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:(XVI)

Coupling between the Boc-aminoacid (VIII) and dipeptide ester (XV) affords the linear tripeptide (XVI). Macrocyclization of (XVI) to produce (XVII) is accomplished by intramolecular olefin metathesis in the presence of Hoveyda's catalyst. Subsequent catalytic hydrogenation of (XVII) leads to a mixture of the desired saturated macrocycle (XIX) and compound (XVIII), produced by hydrogenolysis of the cyclopropane ring. Mitsunobu coupling of (XIX) with methyl 4-hydroxy-7-methoxyquinoline-2-carboxylate (XX) gives rise to quinolinyl ether (XXI). The quinoline carboxylate group of (XXI) is then selectively hydrolyzed by NaOH to furnish the sodium carboxylate salt (XXII).

1 Halmos, T.; Llinas-Brunet, M.; Faucher, A.-M.; Ghiro, E.; Goudreau, N.; Tsantrizos, Y.S.; Cameron, D.R. (Boehringer Ingelheim (Canada) Ltd.); Macrocyclic peptides active against the hepatitis C virus. EP 1169339; JP 2002542160; WO 0059929 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(VIII) 58938 (2S)-2-[(tert-butoxycarbonyl)amino]-8-nonenoic acid C14H25NO4 详情 详情
(XV) 58947 methyl (1R,2S)-1-({[(2S,4R)-4-hydroxypyrrolidinyl]carbonyl}amino)-2-vinylcyclopropanecarboxylate C12H18N2O4 详情 详情
(XVI) 58948 methyl (1R,2S)-1-{[((2S,4R)-1-{(2S)-2-[(tert-butoxycarbonyl)amino]-8-nonenoyl}-4-hydroxypyrrolidinyl)carbonyl]amino}-2-vinylcyclopropanecarboxylate C26H41N3O7 详情 详情
(XVII) 58949 methyl (2R,6S,13aS,16aS)-6-[(tert-butoxycarbonyl)amino]-2-hydroxy-5,16-dioxo-1,2,3,6,7,8,9,10,11,13a,14,15,16,16a-tetradecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a(5H)-carboxylate C24H37N3O7 详情 详情
(XVIII) 58950 methyl (13S,17R,18aS)-13-[(tert-butoxycarbonyl)amino]-17-hydroxy-1,14-dioxooctadecahydropyrrolo[1,2-a][1,4]diazacyclohexadecine-3-carboxylate C24H41N3O7 详情 详情
(XIX) 58951 methyl (2R,6S,13aR,16aS)-6-[(tert-butoxycarbonyl)amino]-2-hydroxy-5,16-dioxohexadecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a(5H)-carboxylate C24H39N3O7 详情 详情
(XX) 58952 methyl 4-hydroxy-7-methoxy-2-quinolinecarboxylate C12H11NO4 详情 详情
(XXI) 58953 methyl (2R,6S,13aR,16aS)-6-[(tert-butoxycarbonyl)amino]-2-{[7-methoxy-2-(methoxycarbonyl)-4-quinolinyl]oxy}-5,16-dioxohexadecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a(5H)-carboxylate C36H48N4O10 详情 详情
(XXII) 58954 sodium 4-{[(2R,6S,13aR,14aR,16aS)-6-[(tert-butoxycarbonyl)amino]-14a-(methoxycarbonyl)-5,16-dioxooctadecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecin-2-yl]oxy}-7-methoxy-2-quinolinecarboxylate C35H45N4NaO10 详情 详情
Extended Information