2-[(3S)-3-[((2R)-3-(benzyloxy)-2-[[(2R)-2-[(2-[[((2R,4S)-1-[[(2R)-1-((2S)-2-([(2S)-6-[[(benzyloxy)carbonyl]amino]-2-[(tert-butoxycarbonyl)amino]hexanoyl]amino)-5-[[imino([[(4-methylphenyl)sulfonyl]oxy]amino)methyl]amino]pentanoyl)pyrrolidinyl]carbon -Drug Synthesis Database

【结构式】

【分子编号】43258

【品名】2-[(3S)-3-[((2R)-3-(benzyloxy)-2-[[(2R)-2-[(2-[[((2R,4S)-1-[[(2R)-1-((2S)-2-([(2S)-6-[[(benzyloxy)carbonyl]amino]-2-[(tert-butoxycarbonyl)amino]hexanoyl]amino)-5-[[imino([[(4-methylphenyl)sulfonyl]oxy]amino)methyl]amino]pentanoyl)pyrrolidinyl]carbon

【CA登记号】

【分子式】C₇₆H₉₅N₁₃O₁₉S₂

【分子量】1558.79852

【元素组成】C 58.56% H 6.14% N 11.68% O 19.5% S 4.11%

与该中间体有关的原料药合成路线共 4 条

合成路线1 合成路线2 合成路线3 合成路线4

合成路线1

该中间体在本合成路线中的序号：(XXV)

The peptidic chain is elongated by successive deprotection with TFA/EDT and coupling of protected amino acids (Boc-Arg(Tos)-OH (XXII), Boc-Lys(COOCH2Ph)-OH (XXIV)) with BOP/DIEA, providing derivative (XXIV). (Scheme 28946801c).

参考文献中间体

合成目标

【1】 Bedos, P.; Daffix, I.; Amblard, M.; et al.; Design and synthesis of potent bradykinin agonists containing a benzothiazepine moiety. J Med Chem 1999, 42, 20, 4185.
【2】 Amblard, M.; Bedos, P.; Olivier, C.; Daffix, I.; Luccarini, J.M.; Dodey, P.; Pruneau, D.; Paquet, J.L.; Martinez, J.; Synthesis and biological evaluation of bradykinin B1/B2 and selective B1 receptor antagonists. J Med Chem 2000, 43, 12, 2382.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(XXI)	43255	2-[(3S)-3-[((2R)-3-(benzyloxy)-2-[[(2R)-2-[(2-[[((2R,4S)-1-[[(2R)-1-(tert-butoxycarbonyl)pyrrolidinyl]carbonyl]-4-hydroxypyrrolidinyl)carbonyl]amino]acetyl)amino]-2-(2,3-dihydro-1H-inden-2-yl)ethanoyl]amino]propanoyl)amino]-4-oxo-3,4-dihydro-1,5-ben	C₄₉H₅₉N₇O₁₂S	详情	详情
(XXII)	43256	(2S)-2-[(tert-butoxycarbonyl)amino]-5-[[imino([[(4-methylphenyl)sulfonyl]oxy]amino)methyl]amino]pentanoic acid	C₁₈H₂₈N₄O₇S	详情	详情
(XXIII)	43257	2-[(3S)-3-[((2R)-3-(benzyloxy)-2-[[(2R)-2-[(2-[[((2R,4S)-1-[[(2R)-1-((2S)-2-[(tert-butoxycarbonyl)amino]-5-[[imino([[(4-methylphenyl)sulfonyl]oxy]amino)methyl]amino]pentanoyl)pyrrolidinyl]carbonyl]-4-hydroxypyrrolidinyl)carbonyl]amino]acetyl)amino]-	C₆₂H₇₇N₁₁O₁₆S₂	详情	详情
(XXIV)	23159	(2S)-6-[[(benzyloxy)carbonyl]amino]-2-[(tert-butoxycarbonyl)amino]hexanoic acid	C₁₉H₂₈N₂O₆	详情	详情
(XXV)	43258	2-[(3S)-3-[((2R)-3-(benzyloxy)-2-[[(2R)-2-[(2-[[((2R,4S)-1-[[(2R)-1-((2S)-2-([(2S)-6-[[(benzyloxy)carbonyl]amino]-2-[(tert-butoxycarbonyl)amino]hexanoyl]amino)-5-[[imino([[(4-methylphenyl)sulfonyl]oxy]amino)methyl]amino]pentanoyl)pyrrolidinyl]carbon	C₇₆H₉₅N₁₃O₁₉S₂	详情	详情

合成路线2

该中间体在本合成路线中的序号：(XXV)

Derivative (XXIV) is finally deprotected and cleaved by a first treatment with TFA/EDT followed by HF in the presence of anisole. (Schemes 28946801d).

参考文献中间体

合成目标

【1】 Bedos, P.; Daffix, I.; Amblard, M.; et al.; Design and synthesis of potent bradykinin agonists containing a benzothiazepine moiety. J Med Chem 1999, 42, 20, 4185.
【2】 Amblard, M.; Bedos, P.; Olivier, C.; Daffix, I.; Luccarini, J.M.; Dodey, P.; Pruneau, D.; Paquet, J.L.; Martinez, J.; Synthesis and biological evaluation of bradykinin B1/B2 and selective B1 receptor antagonists. J Med Chem 2000, 43, 12, 2382.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(XXV)	43258	2-[(3S)-3-[((2R)-3-(benzyloxy)-2-[[(2R)-2-[(2-[[((2R,4S)-1-[[(2R)-1-((2S)-2-([(2S)-6-[[(benzyloxy)carbonyl]amino]-2-[(tert-butoxycarbonyl)amino]hexanoyl]amino)-5-[[imino([[(4-methylphenyl)sulfonyl]oxy]amino)methyl]amino]pentanoyl)pyrrolidinyl]carbon		C₇₆H₉₅N₁₃O₁₉S₂	详情	详情

合成路线3

该中间体在本合成路线中的序号：(XXV)

The peptidic chain is elongated by successive deprotection with TFA/EDT and coupling of protected amino acids (Boc Arg(Tos)-OH (XXII), and Boc-Lys(COOCH2Ph)-OH (XXIV)) with BOP/DIEA, providing derivative (XXV)(Scheme 28947001c).

参考文献中间体

合成目标

【1】 Bedos, P.; Daffix, I.; Amblard, M.; et al.; Design and synthesis of potent bradykinin agonists containing a benzothiazepine moiety. J Med Chem 1999, 42, 20, 4185.
【2】 Amblard, M.; Bedos, P.; Olivier, C.; Daffix, I.; Luccarini, J.M.; Dodey, P.; Pruneau, D.; Paquet, J.L.; Martinez, J.; Synthesis and biological evaluation of bradykinin B1/B2 and selective B1 receptor antagonists. J Med Chem 2000, 43, 12, 2382.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(XXI)	43255	2-[(3S)-3-[((2R)-3-(benzyloxy)-2-[[(2R)-2-[(2-[[((2R,4S)-1-[[(2R)-1-(tert-butoxycarbonyl)pyrrolidinyl]carbonyl]-4-hydroxypyrrolidinyl)carbonyl]amino]acetyl)amino]-2-(2,3-dihydro-1H-inden-2-yl)ethanoyl]amino]propanoyl)amino]-4-oxo-3,4-dihydro-1,5-ben	C₄₉H₅₉N₇O₁₂S	详情	详情
(XXII)	43256	(2S)-2-[(tert-butoxycarbonyl)amino]-5-[[imino([[(4-methylphenyl)sulfonyl]oxy]amino)methyl]amino]pentanoic acid	C₁₈H₂₈N₄O₇S	详情	详情
(XXIII)	43257	2-[(3S)-3-[((2R)-3-(benzyloxy)-2-[[(2R)-2-[(2-[[((2R,4S)-1-[[(2R)-1-((2S)-2-[(tert-butoxycarbonyl)amino]-5-[[imino([[(4-methylphenyl)sulfonyl]oxy]amino)methyl]amino]pentanoyl)pyrrolidinyl]carbonyl]-4-hydroxypyrrolidinyl)carbonyl]amino]acetyl)amino]-	C₆₂H₇₇N₁₁O₁₆S₂	详情	详情
(XXIV)	23159	(2S)-6-[[(benzyloxy)carbonyl]amino]-2-[(tert-butoxycarbonyl)amino]hexanoic acid	C₁₉H₂₈N₂O₆	详情	详情
(XXV)	43258	2-[(3S)-3-[((2R)-3-(benzyloxy)-2-[[(2R)-2-[(2-[[((2R,4S)-1-[[(2R)-1-((2S)-2-([(2S)-6-[[(benzyloxy)carbonyl]amino]-2-[(tert-butoxycarbonyl)amino]hexanoyl]amino)-5-[[imino([[(4-methylphenyl)sulfonyl]oxy]amino)methyl]amino]pentanoyl)pyrrolidinyl]carbon	C₇₆H₉₅N₁₃O₁₉S₂	详情	详情

合成路线4

该中间体在本合成路线中的序号：(XXV)

The peptidic chain is elongated by deprotection with TFA/EDT and coupling of protected amino acid (Boc-Lys(COOCH2Ph)-OH (XXIV)) with BOP/DIEA, providing derivative (XXVI), which is finally deprotected and cleaved by a first treatment with TFA/EDT followed by HF in the presence of anisole (Scheme 28947001d).

参考文献中间体

合成目标

【1】 Bedos, P.; Daffix, I.; Amblard, M.; et al.; Design and synthesis of potent bradykinin agonists containing a benzothiazepine moiety. J Med Chem 1999, 42, 20, 4185.
【2】 Amblard, M.; Bedos, P.; Olivier, C.; Daffix, I.; Luccarini, J.M.; Dodey, P.; Pruneau, D.; Paquet, J.L.; Martinez, J.; Synthesis and biological evaluation of bradykinin B1/B2 and selective B1 receptor antagonists. J Med Chem 2000, 43, 12, 2382.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(XXIV)	23159	(2S)-6-[[(benzyloxy)carbonyl]amino]-2-[(tert-butoxycarbonyl)amino]hexanoic acid	C₁₉H₂₈N₂O₆	详情	详情
(XXV)	43258	2-[(3S)-3-[((2R)-3-(benzyloxy)-2-[[(2R)-2-[(2-[[((2R,4S)-1-[[(2R)-1-((2S)-2-([(2S)-6-[[(benzyloxy)carbonyl]amino]-2-[(tert-butoxycarbonyl)amino]hexanoyl]amino)-5-[[imino([[(4-methylphenyl)sulfonyl]oxy]amino)methyl]amino]pentanoyl)pyrrolidinyl]carbon	C₇₆H₉₅N₁₃O₁₉S₂	详情	详情
(XXVI)	43259	2-[(3S)-3-[((2R)-3-(benzyloxy)-2-[[(2R)-2-[[2-([[(2R,4S)-1-([(2R)-1-[(2S,5S,8S)-5-(4-[[(benzyloxy)carbonyl]amino]butyl)-8-[(tert-butoxycarbonyl)amino]-2-(3-[[imino([[(4-methylphenyl)sulfonyl]oxy]amino)methyl]amino]propyl)-4,7,14-trioxo-16-phenyl-15-	C₉₀H₁₁₃N₁₅O₂₂S₂	详情	详情

Extended Information