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【结 构 式】 
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【分子编号】18001 【品名】methyl 2-nitriloacetate; carbonocyanic acid, methyl ester 【CA登记号】17640-15-2 |
【 分 子 式 】C3H3NO2 【 分 子 量 】85.06236 【元素组成】C 42.36% H 3.55% N 16.47% O 37.62% |
合成路线1
该中间体在本合成路线中的序号：(II)Reaction of tetrabutylammonium [11C]cyanide (I) with methyl chloroformate in a two phase system afforded labeled methyl cyanoformate (II), which was refluxed in ethanolic HCl to yield diethyl [1-11C]oxalate (III).
| 【1】 Thorell, J.O.; et al.; Synthesis of a C-11-labelled nitrated 1,4-dihydroquinoxaline-2,3-dione, the NMDA glycine receptor antagonist ACEA 1021 (Licostinel). J Label Compd Radiopharm 1998, 41, 4, 345-353. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| 16993 | methyl chlorocarbonate;Carbonochloridic acid methyl ester；[(chlorocarbonyl)oxy]methane；methyl chloroformate | 79-22-1 | C2H3ClO2 | 详情 | 详情 | |
| (II) | 18001 | methyl 2-nitriloacetate; carbonocyanic acid, methyl ester | 17640-15-2 | C3H3NO2 | 详情 | 详情 |
| (II) | 45300 | methyl 2-nitriloacetate | C3H3NO2 | 详情 | 详情 | |
| (III) | 17571 | Diethyl oxalate; Ethyl 2-ethoxy-2-oxoacetate | 95-92-1 | C6H10O4 | 详情 | 详情 |
| (III) | 45301 | ethyl 2-ethoxy-2-oxoacetate | C6H10O4 | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(A)Oxidation of 5-hydroxy-5,6,7,8-tetrahydroisoquinoline (I) using CrO3 in pyridine produced the corresponding ketone (II). Subsequent condensation of (II) with methyl cyanoformate (A) in the presence of lithium hexamethyldisilazide gave ketoester (III), which was reduced to hydroxyester (IV) by means of catalytic hydrogenation. Dehydration of (IV) to the unsaturated ester (V) was achieved by treatment with methanesulfonyl chloride and triethylamine, followed by basic elimination with DBU. Saponification of the ester group of (V) produced carboxylic acid (VI). After activation of (VI) as the mixed anhydride (VII) with isopropyl chloroformate (B), coupling with tryptamine (VIII) furnished the title amide, which was finally isolated as the hydrochloride salt.
| 【1】 May, S.; Chan, L.; Chen, Y.; Jin, H.; Hu, Z.; Bedard, J.; Stefanac, T.; Turcotte, N.; Design and evaluation of dihydroisoquinolines as potent and orally bioavailable human cytomegalovirus inhibitors. Bioorg Med Chem Lett 2000, 10, 13, 1477. |
| 【2】 Bedard, J.; Rando, R.; Falardeau, G.; Lavallee, J.-F. (BioChem Pharma Inc.); Antiviral cpds.. WO 9929318 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (A) | 18001 | methyl 2-nitriloacetate; carbonocyanic acid, methyl ester | 17640-15-2 | C3H3NO2 | 详情 | 详情 |
| (B) | 26492 | 2-[(chlorocarbonyl)oxy]propane | 108-23-6 | C4H7ClO2 | 详情 | 详情 |
| (I) | 40530 | 5,6,7,8-tetrahydro-5-isoquinolinol | C9H11NO | 详情 | 详情 | |
| (II) | 40531 | 7,8-dihydro-5(6H)-isoquinolinone | C9H9NO | 详情 | 详情 | |
| (III) | 40532 | methyl 5-hydroxy-7,8-dihydro-6-isoquinolinecarboxylate | C11H11NO3 | 详情 | 详情 | |
| (IV) | 40533 | methyl 5-hydroxy-5,6,7,8-tetrahydro-6-isoquinolinecarboxylate | C11H13NO3 | 详情 | 详情 | |
| (V) | 40534 | methyl 7,8-dihydro-6-isoquinolinecarboxylate | C11H11NO2 | 详情 | 详情 | |
| (VI) | 40535 | 7,8-dihydro-6-isoquinolinecarboxylic acid | C10H9NO2 | 详情 | 详情 | |
| (VII) | 40536 | C14H15NO4 | 详情 | 详情 | ||
| (VIII) | 40537 | Tryptamine; 2-(1H-Indol-3-yl)-1-ethanamine; 2-(1H-Indol-3-yl)ethylamine | 61-54-1 | C10H12N2 | 详情 | 详情 |