(2S)-2-[(3-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-2,2-dimethylpropanoyl)oxy]-4-methylpentanoic acid -Drug Synthesis Database

【结构式】

【分子编号】36507

【品名】(2S)-2-[(3-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-2,2-dimethylpropanoyl)oxy]-4-methylpentanoic acid

【CA登记号】

【分子式】C₂₆H₃₁NO₆

【分子量】453.53528

【元素组成】C 68.86% H 6.89% N 3.09% O 21.17%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(XX)

The deprotection of the carbamate (XVIII) by means of TFA gives the free aminoester (XIX), which is reprotected with Fmoc-Cl and NaHCO3 yielding the acid (XX). The esterification of the hydroxy group of he intermediate (XVII) with the acid group of (XX) by means of EDC affords the expected ester (XXI). The oxidation of the methylsulfanyl group of (XXI) with oxone affords the corresponding methylsulfonylmethyl ester (XXII), which is cyclized by means of piperidine in DMF to give the macrocyclic epoxide (XXIII). Finally, this compound is treated with 12 N HCl in dimethoxyethane/water.

参考文献中间体

合成目标

【1】 Zmijewski, M.J.J.; Zhang, T.Y.; Aikins, J.A.; Briggs, B.S. (Eli Lilly and Company; University of Hawaii; Wayne State University); Stereoselective process for producing antineoplastic agents. WO 0023429 .

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(XVII)	36505	(methylsulfanyl)methyl (2R)-3-(3-chloro-4-methoxyphenyl)-2-([(E,5S,6S)-5-hydroxy-6-[(2R,3S)-3-phenyloxiranyl]-2-heptenoyl]amino)propanoate	C₂₇H₃₂ClNO₆S	详情	详情
(XVIII)	18904	(2S)-2-([3-[(tert-butoxycarbonyl)amino]-2,2-dimethylpropanoyl]oxy)-4-methylpentanoic acid	C₁₆H₂₉NO₆	详情	详情
(XIX)	36506	(2S)-2-[(3-amino-2,2-dimethylpropanoyl)oxy]-4-methylpentanoic acid	C₁₁H₂₁NO₄	详情	详情
(XX)	36507	(2S)-2-[(3-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-2,2-dimethylpropanoyl)oxy]-4-methylpentanoic acid	C₂₆H₃₁NO₆	详情	详情
(XXI)	36508	(methylsulfanyl)methyl (9S,12S,14E,18R)-18-(3-chloro-4-methoxybenzyl)-1-(9H-fluoren-9-yl)-9-isobutyl-6,6-dimethyl-3,7,10,16-tetraoxo-12-[(1R)-1-[(2R,3S)-3-phenyloxiranyl]ethyl]-2,8,11-trioxa-4,17-diaza-14-nonadecen-19-oate	C₅₃H₆₁ClN₂O₁₁S	详情	详情
(XXII)	36509	(methylsulfonyl)methyl (9S,12S,14E,18R)-18-(3-chloro-4-methoxybenzyl)-1-(9H-fluoren-9-yl)-9-isobutyl-6,6-dimethyl-3,7,10,16-tetraoxo-12-[(1R)-1-[(2R,3S)-3-phenyloxiranyl]ethyl]-2,8,11-trioxa-4,17-diaza-14-nonadecen-19-oate	C₅₃H₆₁ClN₂O₁₃S	详情	详情
(XXIII)	63540	(3S,10R,16S)-10-(3-chloro-4-methoxybenzyl)-3-isobutyl-6,6-dimethyl-16-{(1R)-1-[(2R,3R)-3-phenyloxiranyl]ethyl}-1,4-dioxa-8,11-diaza-13-cyclohexadecene-2,5,9,12-tetrone	C₃₆H₄₅ClN₂O₈	详情	详情

合成路线2

该中间体在本合成路线中的序号：(XX)

参考文献中间体

合成目标

【1】 Zmijewski, M.J.J.; Zhang, T.Y.; Aikins, J.A.; Briggs, B.S. (Eli Lilly and Company; University of Hawaii; Wayne State University); Stereoselective process for producing antineoplastic agents. WO 0023429 .

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(XVII)	36505	(methylsulfanyl)methyl (2R)-3-(3-chloro-4-methoxyphenyl)-2-([(E,5S,6S)-5-hydroxy-6-[(2R,3S)-3-phenyloxiranyl]-2-heptenoyl]amino)propanoate	C₂₇H₃₂ClNO₆S	详情	详情
(XVIII)	18904	(2S)-2-([3-[(tert-butoxycarbonyl)amino]-2,2-dimethylpropanoyl]oxy)-4-methylpentanoic acid	C₁₆H₂₉NO₆	详情	详情
(XIX)	36506	(2S)-2-[(3-amino-2,2-dimethylpropanoyl)oxy]-4-methylpentanoic acid	C₁₁H₂₁NO₄	详情	详情
(XX)	36507	(2S)-2-[(3-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-2,2-dimethylpropanoyl)oxy]-4-methylpentanoic acid	C₂₆H₃₁NO₆	详情	详情
(XXI)	36508	(methylsulfanyl)methyl (9S,12S,14E,18R)-18-(3-chloro-4-methoxybenzyl)-1-(9H-fluoren-9-yl)-9-isobutyl-6,6-dimethyl-3,7,10,16-tetraoxo-12-[(1R)-1-[(2R,3S)-3-phenyloxiranyl]ethyl]-2,8,11-trioxa-4,17-diaza-14-nonadecen-19-oate	C₅₃H₆₁ClN₂O₁₁S	详情	详情
(XXII)	36509	(methylsulfonyl)methyl (9S,12S,14E,18R)-18-(3-chloro-4-methoxybenzyl)-1-(9H-fluoren-9-yl)-9-isobutyl-6,6-dimethyl-3,7,10,16-tetraoxo-12-[(1R)-1-[(2R,3S)-3-phenyloxiranyl]ethyl]-2,8,11-trioxa-4,17-diaza-14-nonadecen-19-oate	C₅₃H₆₁ClN₂O₁₃S	详情	详情

Extended Information