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【结 构 式】

【分子编号】57860

【品名】N-Phthalyl-DL-glutamic anhydride; Phthalyl-Dl-Glutamic anhydride

【CA登记号】3085-92-5

【 分 子 式 】C13H9NO5

【 分 子 量 】259.2182

【元素组成】C 60.24% H 3.5% N 5.4% O 30.86%

与该中间体有关的原料药合成路线共 2 条

合成路线1

该中间体在本合成路线中的序号:(II)

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2

该中间体在本合成路线中的序号:(IV)

 

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