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【结 构 式】 
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【分子编号】38582 【品名】1-phenylethyl 3-methyl-2-[(2R,3R)-2-(methylsulfanyl)-4-oxo-3-(tritylamino)azetidinyl]-2-butenoate 【CA登记号】 |
【 分 子 式 】C36H36N2O3S 【 分 子 量 】576.75952 【元素组成】C 74.97% H 6.29% N 4.86% O 8.32% S 5.56% |
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：(II)6-(Tritylamino)penicillanic acid (I) is converted into the azetidinone (II), which is treated with p-toluenesulfonic acid to yield the tosylate (III). The chlorination of (III) with Cl2 in carbon tetrachloride affords the 4-chloroazetidinone (IV), which is condensed with propargyl alcohol (V) by means of AgBF4 in THF to give the propargyl ether (VI) as a mixture of cis and trans isomers that is separated by chromatography. The acylation of (VI) with phenylacetyl chloride (VII) and pyridine affords the amide (VIII).
| 【1】 Narisada, M.; et al.; Synthetic studies on beta-lactam antibiotics. Part 5. A synthesis of 7beta-acylamino-3-methyl-1-oxadethia-3-cephem-4-carboxylic acids. Heterocycles 1977, 7, 2, 839. |
| 【2】 Nagata, W.; Narisada, M. (Shionogi & Co. Ltd.); Arylmalonamido-1-oxadethiacephalosporins. US 4180571 . |
| 【3】 Narisada, M.; Nagata, W. (Shionogi & Co. Ltd.); Arylmalonamido-1-oxadethiacephalosporins. DE 2713370; US 4138486 . |
| 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) | 38581 | Benzhydryl (2S,5R,6R)-3,3-dimethyl-7-oxo-6-(tritylamino)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate | C40H36N2O3S | 详情 | 详情 | |
| (II) | 38582 | 1-phenylethyl 3-methyl-2-[(2R,3R)-2-(methylsulfanyl)-4-oxo-3-(tritylamino)azetidinyl]-2-butenoate | C36H36N2O3S | 详情 | 详情 | |
| (III) | 38583 | 1-phenylethyl 2-[(2R,3R)-3-amino-2-(methylsulfanyl)-4-oxoazetidinyl]-3-methyl-2-butenoate | C17H22N2O3S | 详情 | 详情 | |
| (IV) | 38584 | 1-phenylethyl 2-[(3R)-3-amino-2-chloro-4-oxoazetidinyl]-3-methyl-2-butenoate | C16H19ClN2O3 | 详情 | 详情 | |
| (V) | 16664 | Propargyl Alcohol; 2-propyn-1-ol | 107-19-7 | C3H4O | 详情 | 详情 |
| (VI) | 38585 | 1-phenylethyl 2-[(3S,4R)-3-amino-2-oxo-4-(2-propynyloxy)azetidinyl]-3-methyl-2-butenoate | C19H22N2O4 | 详情 | 详情 | |
| (VII) | 25890 | 2-phenylacetyl chloride；Phenylacetyl chloride;Phenacetyl chloride;Benzeneacetyl chloride | 103-80-0 | C8H7ClO | 详情 | 详情 |
| (VIII) | 38586 | 1-phenylethyl 3-methyl-2-[(3S,4R)-2-oxo-3-[(2-phenylacetyl)amino]-4-(2-propynyloxy)azetidinyl]-2-butenoate | C27H28N2O5 | 详情 | 详情 |
Extended Information