methyl (2R,6S,13aR,16aS)-2-({2-[2-(acetylamino)-1,3-thiazol-4-yl]-7-methoxy-4-quinolinyl}oxy)-6-[(tert-butoxycarbonyl)amino]-5,16-dioxohexadecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a(5H)-carboxylate -Drug Synthesis Database

【结构式】

【分子编号】58959

【品名】methyl (2R,6S,13aR,16aS)-2-({2-[2-(acetylamino)-1,3-thiazol-4-yl]-7-methoxy-4-quinolinyl}oxy)-6-[(tert-butoxycarbonyl)amino]-5,16-dioxohexadecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a(5H)-carboxylate

【CA登记号】

【分子式】C₃₉H₅₀N₆O₉S

【分子量】778.92704

【元素组成】C 60.14% H 6.47% N 10.79% O 18.49% S 4.12%

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：(XXVII)

The sodium carboxylate (XXII) is activated as the mixed anhydride (XXIII) by treatment with isobutyl chloroformate and triethylamine. Subsequent addition of diazomethane to the mixed anhydride (XXIII) leads to diazo ketone (XXIV), which is further transformed into bromo ketone (XXV) upon treatment with HBr. Cyclization of bromo ketone (XXV) with N-acetyl thiourea (XXVI) produces the thiazole derivative (XXVII). The methyl ester group of (XXVII) is finally hydrolyzed by means of LiOH to the target carboxylic acid.

参考文献中间体

合成目标

【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
(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
(XXIII)	58955			C₄₀H₅₄N₄O₁₂	详情	详情
(XXIV)	58956			C₃₆H₄₆N₆O₉	详情	详情
(XXV)	58957	methyl (2R,6S,13aR,16aS)-2-{[2-(2-bromoacetyl)-7-methoxy-4-quinolinyl]oxy}-6-[(tert-butoxycarbonyl)amino]-5,16-dioxohexadecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a(5H)-carboxylate		C₃₆H₄₇BrN₄O₉	详情	详情
(XXVI)	58958	1-Acetyl-2-thiourea; N-Acetylthiourea	591-08-2	C₃H₆N₂OS	详情	详情
(XXVII)	58959	methyl (2R,6S,13aR,16aS)-2-({2-[2-(acetylamino)-1,3-thiazol-4-yl]-7-methoxy-4-quinolinyl}oxy)-6-[(tert-butoxycarbonyl)amino]-5,16-dioxohexadecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a(5H)-carboxylate		C₃₉H₅₀N₆O₉S	详情	详情

Extended Information