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【结 构 式】 
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【分子编号】26568 【品名】2-[N,N-Bis[2-[N,N-bis(tert-butoxycarbonylmethyl)amino]ethyl]amino]-6-[N-(4-pentylbicyclo[2,2,2]oct-1-ylcarbonyl)-(4-O-tert-butyl)-L-aspartyl-(4-O-tert-butyl)-L-aspartylamino]hexanoic acid tert-butyl ester; 2-[N,N-Bis[2-[N,N-bis(tert-butoxycarbonylmethyl)amino]ethyl]amino]-6-[N-(4-pentylbicyclo[2,2,2]oct-1-ylcarbonyl)-(4-O-tert-butyl)-L-aspartyl-(4-O-tert-butyl)-L-aspartylamino]hexanoic acid tert-butyl ester 【CA登记号】 |
【 分 子 式 】C68H120N6O17 【 分 子 量 】1293.73104 【元素组成】C 63.13% H 9.35% N 6.5% O 21.02% |
合成路线1
该中间体在本合成路线中的序号：(VI)4-Pentylbicyclo[2.2.2]octane-1-carboxylic acid (I) was converted to the corresponding acid chloride with SOCl2 and then coupled to L-aspartic acid beta-tert-butyl ester (II) to afford amide (III). Subsequent coupling of (III) with further L-aspartic acid beta-tert-butyl ester (II) in the presence of DCC and NHS produced diamide (IV). This was then condensed with (aminobutyl)diethylenetriamino-pentaacetic acid penta-tert-butyl ester (V) to provide (VI).
| 【1】 Wallace, R.A.; Haar, J.P. Jr.; Miller, D.B.; Woulfe, S.R.; Polta, J.A.; Galen, K.P.; Hynes, M.R.; Adzamli, K.; Synthesis and preliminary evaluation of MP-2269: A novel, nonaromatic small-molecule blood-pool MR contrast agent. Magn Reson Med 1998, 40, 5, 733. |
| 【2】 Woulfe, S.R. (Mallinckrodt Medical Inc.); Magnetic resonance blood pool agents. WO 9820908 . |
| 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) | 26563 | 4-pentylbicyclo[2.2.2]octane-1-carboxylic acid | C14H24O2 | 详情 | 详情 | |
| (II) | 26564 | (2S)-2-amino-4-(tert-butoxy)-4-oxobutyric acid | 3057-74-7 | C8H15NO4 | 详情 | 详情 |
| (III) | 26565 | (2S)-4-(tert-butoxy)-4-oxo-2-[[(4-pentylbicyclo[2.2.2]oct-1-yl)carbonyl]amino]butyric acid | C22H37NO5 | 详情 | 详情 | |
| (IV) | 26566 | (2S)-4-(tert-butoxy)-2-[((2S)-4-(tert-butoxy)-4-oxo-2-[[(4-pentylbicyclo[2.2.2]oct-1-yl)carbonyl]amino]butanoyl)amino]-4-oxobutyric acid | C30H50N2O8 | 详情 | 详情 | |
| (V) | 26567 | tert-butyl 9-[5-amino-1-(tert-butoxycarbonyl)pentyl]-6,12-bis[2-(tert-butoxy)-2-oxoethyl]-2,2-dimethyl-4-oxo-3-oxa-6,9,12-triazatetradecan-14-oate | C38H72N4O10 | 详情 | 详情 | |
| (VI) | 26568 | 2-[N,N-Bis[2-[N,N-bis(tert-butoxycarbonylmethyl)amino]ethyl]amino]-6-[N-(4-pentylbicyclo[2,2,2]oct-1-ylcarbonyl)-(4-O-tert-butyl)-L-aspartyl-(4-O-tert-butyl)-L-aspartylamino]hexanoic acid tert-butyl ester; 2-[N,N-Bis[2-[N,N-bis(tert-butoxycarbonylmethyl)amino]ethyl]amino]-6-[N-(4-pentylbicyclo[2,2,2]oct-1-ylcarbonyl)-(4-O-tert-butyl)-L-aspartyl-(4-O-tert-butyl)-L-aspartylamino]hexanoic acid tert-butyl ester | C68H120N6O17 | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(VI)After deprotection of the tert-butyl ester groups of (VI) with HCl in dioxan, the resulting heptacarboxylic acid (VII) was treated with gadolinium (III) oxide at a controlled pH value to furnish the target gadolinium chelate.
| 【1】 Wallace, R.A.; Haar, J.P. Jr.; Miller, D.B.; Woulfe, S.R.; Polta, J.A.; Galen, K.P.; Hynes, M.R.; Adzamli, K.; Synthesis and preliminary evaluation of MP-2269: A novel, nonaromatic small-molecule blood-pool MR contrast agent. Magn Reson Med 1998, 40, 5, 733. |
| 【2】 Woulfe, S.R. (Mallinckrodt Medical Inc.); Magnetic resonance blood pool agents. WO 9820908 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (VI) | 26568 | 2-[N,N-Bis[2-[N,N-bis(tert-butoxycarbonylmethyl)amino]ethyl]amino]-6-[N-(4-pentylbicyclo[2,2,2]oct-1-ylcarbonyl)-(4-O-tert-butyl)-L-aspartyl-(4-O-tert-butyl)-L-aspartylamino]hexanoic acid tert-butyl ester; 2-[N,N-Bis[2-[N,N-bis(tert-butoxycarbonylmethyl)amino]ethyl]amino]-6-[N-(4-pentylbicyclo[2,2,2]oct-1-ylcarbonyl)-(4-O-tert-butyl)-L-aspartyl-(4-O-tert-butyl)-L-aspartylamino]hexanoic acid tert-butyl ester | C68H120N6O17 | 详情 | 详情 | |
| (VII) | 26569 | 2-[N,N-Bis[2-[N,N-bis(carboxymethyl)amino]ethyl]amino]-6-[N-(4-pentylbicyclo[2,2,2]oct-1-ylcarbonyl)-L-aspartyl-L-aspartylamino]hexanoic acid; 2-[N,N-Bis[2-[N,N-bis(carboxymethyl)amino]ethyl]amino]-6-[N-(4-pentylbicyclo[2,2,2]oct-1-ylcarbonyl)-L-aspartyl-L-aspartylamino]hexanoic acid | C40H64N6O17 | 详情 | 详情 |