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【结 构 式】 
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【分子编号】20865 【品名】3-iodobenzylamine; (3-iodophenyl)methanamine 【CA登记号】 |
【 分 子 式 】C7H8IN 【 分 子 量 】233.05173 【元素组成】C 36.08% H 3.46% I 54.45% N 6.01% |
合成路线1
该中间体在本合成路线中的序号：(I)MIBG is synthesized as follows: A mixture of m-iodobenzylamine (I) hydrochloride and cyanamide (II) is stirred and heated at 100 C for 4h. The resulting m-iodobenzylguanidine is converted to the bicarbonate salt by treatment with aqueous potassium bicarbonate. Addition of dilute sulfuric acid gives the guanidine sulfate. To prepare the labeled compound, the unlabeled m-iodobenzylguanidinium sulfate is dissolved in water and treated with carrier-free Na[131]I. Refluxing for 72h and passage through Cellex D anion exchange cellulose gives [131]iodobenzylguanidine sulfate. Another more efficient method of carrying out the exchange-labeling step has been reported.
| 【1】 Eastland, G. Jr.; Iobenguane (131I). Drugs Fut 1989, 14, 5, 427. |
| 【2】 Wieland, D.M.; Wu, J.-L.; Brown, L.E.; Mengner, T.J.; Swanson, D.P.; Beierwaltes, W.H.; Radiolabeled adrenergic neuron-blocking agents: Adrenomedullary imaging with [131]iodobenzylguanidine. J Nucl Med 1980, 21, 349-53. |
| 【3】 Shapiro, B.; Copp, J.E.; Sisson, J.C.; Eyres, P.L.; Wallis, J.; Beierwaltes, W.H.; Iodine-131-m-iodobenzylguanidine for the locating of suspected pheochromocytoma: Experience in 400 cases. J Nucl Med 1985, 26, 576-85. |
合成路线2
该中间体在本合成路线中的序号：(VI)7-Aminocephalosporanic acid (I) was converted to tert-butyl ester (II) by treatment with isobutylene and sulfuric acid. Subsequent diazotization, followed by reaction with methanol and rhodium catalyst, provided the 7-methoxy derivative (IIIa-b) as a diastereomeric mixture. The desired 7S-isomer was then deprotected with trifluoroacetic acid in anisole, yielding carboxylic acid (IV). Coupling of acid (IV) with 3-iodobenzylamine (VI) via activation as the mixed anhydride (V) with ethyl chloroformate gave rise to amide (VII). The sulfide group of (VII) was finally converted into the title sulfone by oxidation with oxone.
| 【1】 Levy, M.A.; Gleason, J.G. (SmithKline Beecham plc); Interleukin converting enzyme and apoptosis. EP 0851760; JP 1999514345; WO 9707805 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (IIIa) | 43145 | tert-butyl (6R,7R)-3-[(acetoxy)methyl]-7-methoxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate | C15H21NO6S | 详情 | 详情 | |
| (IIIb) | 43146 | tert-butyl (6R,7S)-3-[(acetoxy)methyl]-7-methoxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate | C15H21NO6S | 详情 | 详情 | |
| (I) | 22747 | (6R,7R)-3-[(acetoxy)methyl]-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid | C10H12N2O5S | 详情 | 详情 | |
| (II) | 32660 | tert-butyl (6R,7R)-3-[(acetoxy)methyl]-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate | C14H20N2O5S | 详情 | 详情 | |
| (IV) | 43147 | (6R,7S)-3-[(acetoxy)methyl]-7-methoxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid | C11H13NO6S | 详情 | 详情 | |
| (V) | 43148 | C14H17NO8S | 详情 | 详情 | ||
| (VI) | 20865 | 3-iodobenzylamine; (3-iodophenyl)methanamine | C7H8IN | 详情 | 详情 | |
| (VII) | 43149 | ((6R,7S)-2-[[(3-iodobenzyl)amino]carbonyl]-7-methoxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl)methyl acetate | C18H19IN2O5S | 详情 | 详情 |