【结 构 式】 |
【分子编号】38378 【品名】dibenzyl 3,12-bis[2-(benzyloxy)-2-oxoethyl]-6,9-bis(2-hydroxyethyl)-4,11-dioxo-3,6,9,12-tetraazatetradecane-1,14-dioate 【CA登记号】 |
【 分 子 式 】C46H54N4O12 【 分 子 量 】854.95452 【元素组成】C 64.62% H 6.37% N 6.55% O 22.46% |
合成路线1
该中间体在本合成路线中的序号:(III)The condensation of 2-bromo-N,N-bis(benzyloxycarbonylmethyl)acetamide (I) with N,N'-bis(2-hydroxyethyl)ethylene-1,2-diamine (II) by means of TEA in DMF gives the corresponding bis-adduct (III). The monoacylation of (III) with butyryl chloride (IV) and DMAP in THF yields the monobutyrate (V), which is acylated with acetyl chloride (VI) and DMAP in THF affording the mixed diester monoacetate monobutyrate (VII). The deprotection of (VII) by hydrogenation with H2 over Pd/C in ethanol provides the tetraacetic acid (VIII), which is finally treated with gadolinium trichloride and NaOH to furnish the target compound.
【1】 Saab-Ismail, N.H.; et al.; Synthesis and in vivo evaluation of new contrast agents for cardiac MRI. J Med Chem 1999, 42, 15, 2852. |
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) | 38376 | benzyl 2-[[2-(benzyloxy)-2-oxoethyl](2-bromoacetyl)amino]acetate | C20H20BrNO5 | 详情 | 详情 | |
(II) | 38377 | 2-([2-[(2-hydroxyethyl)amino]ethyl]amino)-1-ethanol | 4439-20-7 | C6H16N2O2 | 详情 | 详情 |
(III) | 38378 | dibenzyl 3,12-bis[2-(benzyloxy)-2-oxoethyl]-6,9-bis(2-hydroxyethyl)-4,11-dioxo-3,6,9,12-tetraazatetradecane-1,14-dioate | C46H54N4O12 | 详情 | 详情 | |
(IV) | 10792 | Butanoyl chloride; Butyryl chloride | 141-75-3 | C4H7ClO | 详情 | 详情 |
(V) | 38379 | dibenzyl 3,12-bis[2-(benzyloxy)-2-oxoethyl]-6-[2-(butyryloxy)ethyl]-9-(2-hydroxyethyl)-4,11-dioxo-3,6,9,12-tetraazatetradecane-1,14-dioate | C50H60N4O13 | 详情 | 详情 | |
(VI) | 19273 | acetyl chloride | 75-36-5 | C2H3ClO | 详情 | 详情 |
(VII) | 38380 | dibenzyl 6-[2-(acetoxy)ethyl]-3,12-bis[2-(benzyloxy)-2-oxoethyl]-9-[2-(butyryloxy)ethyl]-4,11-dioxo-3,6,9,12-tetraazatetradecane-1,14-dioate | C52H62N4O14 | 详情 | 详情 | |
(VIII) | 38381 | 6-[2-(acetoxy)ethyl]-9-[2-(butyryloxy)ethyl]-3,12-bis(carboxymethyl)-4,11-dioxo-3,6,9,12-tetraazatetradecane-1,14-dioic acid | C24H38N4O14 | 详情 | 详情 |