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【结 构 式】 
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【分子编号】24945 【品名】N-[3-(dimethylamino)propyl]-N'-ethylcarbodiimide 【CA登记号】25952-53-8 |
【 分 子 式 】C8H17N3 【 分 子 量 】155.2432 【元素组成】C 61.9% H 11.04% N 27.07% |
合成路线1
该中间体在本合成路线中的序号：(IV)This compound can be obtained by two differents ways: 1) By condensation of 6-allyl-N-[3-(dimethylamino)propyl]ergolin-8-beta-caboxamide (I) with ethyl isocyanate (II) in refluxing toluene. 2) By condensation of 6-allylergolin-8-beta-carboxylic acid (III) with N-ethyl-N'-[3-(dimethylamino)propyl]carbodiimide (IV) in refluxing THF.
| 【1】 Temperilli, A.; Bernardi, L.; Brambilla, E. (Pharmacia Corp.); Regiospecific process for the preparation of ergoline derivatives. BE 0894060; JP 58038282 . |
| 【2】 Salvati, P.; et al. (Pharmacia & Upjohn SpA); Composés dérivés de l'ergoline, procédé pour les préparer et leur usage comme médicaments. DE 3112861; FR 2479829 . |
| 【3】 Serradell, M.N.; Azccheo, T.; Castaner, J.; Castaner, R.M.; Giudici, D.; Cabergoline. Drugs Fut 1987, 12, 9, 842. |
| 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) | 11276 | (6aR,9R,10aR)-7-allyl-N-[3-(Dimethylamino)propyl]-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxamide | C23H32N4O | 详情 | 详情 | |
| (II) | 28738 | ethyl isocyanate | 109-90-0 | C3H5NO | 详情 | 详情 |
| (III) | 28739 | (6aR,9R,10aR)-7-allyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxylic acid | C18H20N2O2 | 详情 | 详情 | |
| (IV) | 24945 | N-[3-(dimethylamino)propyl]-N'-ethylcarbodiimide | 25952-53-8 | C8H17N3 | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(A)Antineoplaston AS2-5 (AS2-5) can be obtained in the following way (1,2): N-Phenylacetyl-L-glutamine sodium is synthesized in two steps. In the first step, phenylacetic acid (I) is treated with N-hydroxysuccinimide (B) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (A) in acetonitrile to give intermediate (Ia). In the second step, (Ia) is reacted without purification with L-glutamine (II) in the presence of NaHCO3 in 1:1 acetonitrile-water mixture to afford N-phenylacetyl-L-glutamine (III) in 87% yield. Compound (III) is then converted to sodium salt in aqueous solution by treatment with aqueous sodium hydroxide solution (pH 7). In a large scale preparation reaction of phenylacetyl chloride with L-glutamine in aqueous solution containing NaHCO3 affords N-phenyiacetyl L-glutamine sodium.
| 【1】 Burzynski, S.R. (Burzynski Research Institute); Purified antineoplaston fractions and methods of treating neoplastic disease. US 4558057 . |
| 【2】 Berman, E.M.; Gregor, V.E.; Showalter, H.H.D. (Pfizer Inc.); Benzoselenino[4,3,2-cd]indazole compound, compositions comprising the compounds and processes for producing the compounds. AU 8544154; EP 0170412; ES 8704956 . |
| 【3】 Khalid, M.; Burzynski, S.R.; Antineoplaston AS2-5. Drugs Fut 1986, 11, 5, 364. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (B) | 10264 | 1-Hydroxydihydro-1H-pyrrole-2,5-dione; N-Hydroxysuccinimide; 1-Hydroxy-2,5-pyrrolidinedione | 6066-82-6 | C4H5NO3 | 详情 | 详情 |
| (Ia) | 24927 | tert-butyl (2R,3aR,7aR,10aR)-8-(dimethoxymethyl)-5-(5-hexenyl)-10-oxo-2-vinyl-2,3,5,6,7,7a,10,10a-octahydropyrrolo[2,3-i]isoquinoline-1(4H)-carboxylate | C27H42N2O5 | 详情 | 详情 | |
| (A) | 24945 | N-[3-(dimethylamino)propyl]-N'-ethylcarbodiimide | 25952-53-8 | C8H17N3 | 详情 | 详情 |
| (I) | 16148 | Benzeneacetic acid; 2-Phenylacetic acid; Phenyl Acetic Acid | 103-82-2 | C8H8O2 | 详情 | 详情 |
| (II) | 24948 | L-glutamine | 56-85-9 | C5H10N2O3 | 详情 | 详情 |
| (III) | 24949 | (2S)-5-amino-5-oxo-2-[(2-phenylacetyl)amino]pentanoic acid | C13H16N2O4 | 详情 | 详情 |