2-[4,10-bis(1-carboxy-4-hydroxy-4-oxobutyl)-7-(1,3-dicarboxypropyl)-1,4,7,10-tetraazacyclododecan-1-yl]pentanedioic acid -Drug Synthesis Database

【结构式】

【分子编号】56043

【品名】2-[4,10-bis(1-carboxy-4-hydroxy-4-oxobutyl)-7-(1,3-dicarboxypropyl)-1,4,7,10-tetraazacyclododecan-1-yl]pentanedioic acid

【CA登记号】

【分子式】C₂₈H₄₄N₄O₁₆

【分子量】692.67472

【元素组成】C 48.55% H 6.4% N 8.09% O 36.96%

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：(IV)

Alkylation of tetraazacyclodecane (I) with ethyl 2-bromobutyrate (II) afforded the tetrasubstituted macrocycle (III) as a mixture of diastereoisomers. Subsequent hydrolysis of the ethyl ester groups of (III) using ethanolic NaOH gave the octacarboxylic acid (IV). Complexation of (IV) with either Gd2O3 or GdCl3 and NaOH generated the corresponding gadolinium chelate. The mixture of diastereoisomeric chelates was then isomerized under acidic conditions to furnish the racemic pair of R,R,R,R and S,S,S,S isomers (V).

参考文献中间体

合成目标

【1】 Port, M.; et al.; P792: A rapid clearance blood pool agent for magnetic resonance imaging: Preliminary results. MAGMA Magn Reson Mater Phys Biol Med 2001, 12, 2-3, 121.
【2】 Rousseaux, O.; Simonot, C. (Guerbet SA); Gadolinium complex tetramides and use in medical imaging. EP 1178975; FR 2793795; WO 0071526 .

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)	14855	1,4,7,10-tetraazacyclododecane; Cyclen	294-90-6	C₈H₂₀N₄	详情	详情
(II)	56041	diethyl 2-bromopentanedioate		C₉H₁₅BrO₄	详情	详情
(III)	56042	diethyl 2-{4,7,10-tris[4-ethoxy-1-(ethoxycarbonyl)-4-oxobutyl]-1,4,7,10-tetraazacyclododecan-1-yl}pentanedioate		C₄₄H₇₆N₄O₁₆	详情	详情
(IV)	56043	2-[4,10-bis(1-carboxy-4-hydroxy-4-oxobutyl)-7-(1,3-dicarboxypropyl)-1,4,7,10-tetraazacyclododecan-1-yl]pentanedioic acid		C₂₈H₄₄N₄O₁₆	详情	详情
(V)	56044	gadolinium (2R)-2-{4,10-bis[(1R)-3-carboxy-1-carboxylatopropyl]-7-[(1R)-1-carboxy-4-hydroxy-4-oxobutyl]-1,4,7,10-tetraazacyclododecan-1-yl}-4-carboxybutanoate		C₂₈H₄₁GdN₄O₁₆	详情	详情

合成路线2

该中间体在本合成路线中的序号：(IV)

In a related synthetic route, the glycinamide derivative (XV) was coupled to acid (IV), and the resultant macrocyclic tetramide was subsequently complexed with GdCl3 to form the title gadolinium chelate.

参考文献中间体

合成目标

【1】 Port, M.; et al.; P792: A rapid clearance blood pool agent for magnetic resonance imaging: Preliminary results. MAGMA Magn Reson Mater Phys Biol Med 2001, 12, 2-3, 121.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(IV)	56043	2-[4,10-bis(1-carboxy-4-hydroxy-4-oxobutyl)-7-(1,3-dicarboxypropyl)-1,4,7,10-tetraazacyclododecan-1-yl]pentanedioic acid		C₂₈H₄₄N₄O₁₆	详情	详情
(XV)	56051	5-[(2-{[4-({4-[(2-aminoacetyl)amino]benzoyl}amino)benzoyl]amino}acetyl)amino]-2,4,6-tribromo-N~1~,N~1~,N~3~,N~3~-tetrakis(2,3,4,5,6-pentahydroxyhexyl)isophthalamide		C₅₀H₇₀Br₃N₇O₂₆	详情	详情

Extended Information