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【结 构 式】 
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【分子编号】54082 【品名】2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)pentanedioic acid 【CA登记号】2301-52-2 |
【 分 子 式 】C13H11NO6 【 分 子 量 】277.23348 【元素组成】C 56.32% H 4% N 5.05% O 34.63% |
与该中间体有关的原料药合成路线共 3 条
合成路线1
该中间体在本合成路线中的序号：(I)A new direct synthesis of thalidomide has been reported: Reaction of the commercially available N-phthaloyl-L-glutamic acid (I) with either urea (II) or thiourea (III) under microwave irradiation (1000 W output) provides thalidomide in 63 or 85% yield, respectively.
| 【1】 Vazquez-Tato, M.P.; Pacios-Lopez, B.; Martinez, M.M.; Gonzalez-Bando, C.; Seijas, J.A.; Microwave promoted synthesis of a rehabilitated drug: Thalidomide. Synthesis (Stuttgart) 2001, 7, 999. |
合成路线2
该中间体在本合成路线中的序号：(I)The reaction of 2-(phthalimido)glutaric acid (I) with acetic anhydride and SOCl2 gives 2-(phthalimido)glutaric anhydride (II), which is treated with urea at 180 C to yield the target thalidomide. Alternatively, anhydride (II) can also be treated with ammonia in dioxane at 180 C in a pressure vessel.
| 【1】 (Grunenthal GmbH); Novel products of the amino-piperidine-2,6-dione series. GB 0768821 . |
| 【2】 Frankus, E.; Graudums, I.; Muckter, H. (Grunenthal GmbH); Derivs. of phthalimidines. GB 1185273 . |
| 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) | 54082 | 2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)pentanedioic acid | 2301-52-2 | C13H11NO6 | 详情 | 详情 |
| (II) | 57860 | N-Phthalyl-DL-glutamic anhydride; Phthalyl-Dl-Glutamic anhydride | 3085-92-5 | C13H9NO5 | 详情 | 详情 |
| (III) | 57861 | (+/-)-N-(2,6-Dioxo-3-piperidinyl)phthalimide; (+/-)-Thalidomide; (?-N-(2,6-Dioxo-3-piperidinyl)phthalimide; Thalidomide | 50-35-1 | C13H10N2O4 | 详情 | 详情 |
合成路线3
该中间体在本合成路线中的序号：(III)
| 【1】 Qian SS, Wu XY, Li JY, et al.2006. Preparation of D-glutamine from glutanuc acid. 有机化学．26(4)：514～517 |
| 【2】 King EE, Kidd DAA. 1949. New synthesis of glutamine and of -dipeptides of glutamic acid from phthalylated intermediates. J Chem Soc, (1949): 3315 - 3319 |
| 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) | 11900 | 2-Benzofuran-1,3-dione;1,2-Benzenedicarboxylic Anhydride;1,2-BENZENE DICARBOXYLIC ACID ANHYDRIDE;1,2-BENZENEDICARBONIC ACID, ANHYDRIDE;1,3-DIOXOPHTHALAN;1,3-ISOBENZOFURANDIONE;o-phthalic anhydride; Phthalic anhydride | 85-44-9 | C8H4O3 | 详情 | 详情 |
| (II) | 28752 | DL-2-Amino propane dicarboxylic acid; DL-2-Aminopentanoic acid; glutamic acid; DL-glutamic acid; (+/-)-2-Aminoglutaric acid | 617-65-2 | C5H9NO4 | 详情 | 详情 |
| (III) | 54082 | 2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)pentanedioic acid | 2301-52-2 | C13H11NO6 | 详情 | 详情 |
| (IV) | 57860 | N-Phthalyl-DL-glutamic anhydride; Phthalyl-Dl-Glutamic anhydride | 3085-92-5 | C13H9NO5 | 详情 | 详情 |
| (V) | 66455 | 5-amino-2-(1,3-dioxoisoindolin-2-yl)-5-oxopentanoic acid | C13H12N2O5 | 详情 | 详情 |
Extended Information