【结 构 式】 |
【分子编号】49101 【品名】Cyclopentylacetic acid 【CA登记号】1123-00-8 |
【 分 子 式 】C7H12O2 【 分 子 量 】128.17108 【元素组成】C 65.6% H 9.44% O 24.97% |
与该中间体有关的原料药合成路线共 1 条
合成路线1
该中间体在本合成路线中的序号:(IX)After conversion of cyclopentylacetic acid (IX) to the corresponding benzyl ester (X), alkylation with 1,8-diiodooctane in the presence of LDA generated the iodo ester (XI). Iodide displacement in (XI) with potassium phthalimide (XII) in hot DMF produced the substituted phthalimide (XIII). Then, hydrogenolysis of the benzyl ester group of (XIII) furnished carboxylic acid (XIV). Acylation of the intermediate dipeptide (VIII) with acid (XIV) by using BOP and HOBt yielded amide (XV). Finally, acid hydrolysis of the diethyl acetal function of (XV) gave rise to the title aldehyde.
【1】 Iqbal, M.; et al.; Potent inhibitors of proteasome. J Med Chem 1995, 38, 13, 2276. |
【2】 Iqbal, M.; Diebold, J.; Siman, R.; Chatterjee, S.; Kauer, J.C. (Cephalon, Inc.); Multicatalytic protease inhibitors. JP 1998507465; JP 2000290197; WO 9614857 . |
中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
---|---|---|---|---|---|---|
(VIII) | 49100 | C16H34N6O5 | 详情 | 详情 | ||
(IX) | 49101 | Cyclopentylacetic acid | 1123-00-8 | C7H12O2 | 详情 | 详情 |
(X) | 49102 | benzyl 2-cyclopentylacetate | C14H18O2 | 详情 | 详情 | |
(XI) | 49103 | benzyl 2-cyclopentyl-10-iododecanoate | C22H33IO2 | 详情 | 详情 | |
(XII) | 27890 | Potassium phthalimide | 1074-82-4 | C8H4KNO2 | 详情 | 详情 |
(XIII) | 49104 | benzyl 2-cyclopentyl-10-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)decanoate | C30H37NO4 | 详情 | 详情 | |
(XIV) | 49105 | 2-cyclopentyl-10-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)decanoic acid | C23H31NO4 | 详情 | 详情 | |
(XV) | 49106 | C39H63N7O8 | 详情 | 详情 |
Extended Information