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【结 构 式】 
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【分子编号】36229 【品名】1-(methylsulfonyl)-2-imidazolidinone 【CA登记号】41730-79-4 |
【 分 子 式 】C4H8N2O3S 【 分 子 量 】164.1852 【元素组成】C 29.26% H 4.91% N 17.06% O 29.23% S 19.53% |
合成路线1
该中间体在本合成路线中的序号：(VI)C-10213-Go has been synthesized from 1-methyl-2-mercaptoimidazole (I). When (I) is methylated with methyl iodide it gives the corresponding thiomethyl derivative (II). Nitration of (II) yields the nitro derivative (III). Oxidation of (III) with monoperphthalic acid gives the sulfone (IV). Condensation of (IV) with 1-methanesulfonyl-2-imidazolidinone (VI) in the presence of sodium hydride affords C-10213-Go.
| 【1】 Arya, V.P.; Satranidazole. Drugs Fut 1983, 8, 9, 797. |
| 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) | 13467 | Methanesulfonyl chloride;Mesyl chloride;Methylsulfonyl chloride;Methanesulfonic acid chloride;Methanesulfonyl chloride;Methanesulphonyl chloride | 124-63-0 | CH3ClO2S | 详情 | 详情 |
| (A) | 34077 | 2-carboperoxybenzoic acid | C8H6O5 | 详情 | 详情 | |
| (I) | 18783 | 1-methyl-1H-imidazol-2-ylhydrosulfide; 1-methyl-1H-imidazole-2-thiol | 60-56-0 | C4H6N2S | 详情 | 详情 |
| (II) | 36225 | 1-methyl-2-(methylsulfanyl)-1H-imidazole; methyl 1-methyl-1H-imidazol-2-yl sulfide | C5H8N2S | 详情 | 详情 | |
| (III) | 36226 | methyl 1-methyl-5-nitro-1H-imidazol-2-yl sulfide; 1-methyl-2-(methylsulfanyl)-5-nitro-1H-imidazole | C5H7N3O2S | 详情 | 详情 | |
| (IV) | 36227 | 1-methyl-2-(methylsulfonyl)-5-nitro-1H-imidazole; methyl 1-methyl-5-nitro-1H-imidazol-2-yl sulfone | C5H7N3O4S | 详情 | 详情 | |
| (V) | 36228 | 2-imidazolidinone | 120-93-4 | C3H6N2O | 详情 | 详情 |
| (VI) | 36229 | 1-(methylsulfonyl)-2-imidazolidinone | 41730-79-4 | C4H8N2O3S | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(VIII)Compound can be prepared in two different ways: 1) By condensation of ampicilline (aminobenzylpenicilline) (I) with 1-chlorocarbonyl-2-oxo-3-mehylsulfonylimidazolidine (II) by means of NaOH in cool water or triethylamine in THF-water. 2) By condensation of 6-aminopenicillanic acid (III) with D-[(3-methylsulfonyl-2-oxoimidazolidin-1-yl)carbonylamino]phenylacetic acid (IV) by means of tetramethylchloroformamidinium chloride (A) and N-methylmorpholine (B) in methylene chloride - THF. The phenylacetic acid (IV) is obtained by condensation of D-phenylglycine (V) with 1-chlorocarbonyl-2-oxo-3-mehylsulfonylimidazolidine (II) by means of NaOH in dioxane - water. The acid chloride (II) is prepared by reaction of 2-imidazolidone (VI) with methanesulfonyl chloride (VII) in refluxing THF to give N-methylsulfonyl-2-imidazolidone (VIII), which is then condensed with phosgene by means of trimethylchlorosilane and triethylamine in dioxane.
| 【1】 Koenig, H.B.; et al.; Penicillin compounds their production and their medicinal use. DE 2152968; FR 2157909; GB 1392850; JP 48049788; JP 48049911 . |
| 【2】 Koenig, H.B.; et al.; Penicillins their production and their medicinal use. DE 2152967; FR 2157908; GB 1392849; JP 48049787; JP 48049910 . |
| 【3】 Schroeck, W.; et al.; Penicillanic acids their production and their medicinal use. DE 2318955; ES 425197; FR 2225151; GB 1465355; JP 49135990 . |
| 【4】 Playle, A.C.; Castañer, J.; Mezlocillin. Drugs Fut 1977, 2, 9, 600. |
| 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) | 28928 | 4-methylmorpholine | 109-02-4 | C5H11NO | 详情 | 详情 |
| (A) | 40169 | N-[chloro(dimethylamino)methylene]-N-methylmethanaminium chloride | C5H12Cl2N2 | 详情 | 详情 | |
| (I) | 31107 | (2S,5R,6R)-6-[[(2R)-2-amino-2-phenylethanoyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid | 69-53-4 | C16H19N3O4S | 详情 | 详情 |
| (II) | 40167 | 3-(methylsulfonyl)-2-oxo-1-imidazolidinecarbonyl chloride | 41762-76-9 | C5H7ClN2O4S | 详情 | 详情 |
| (III) | 32631 | (2S,5R,6R)-6-amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; (+)-6-Aminopenicillanic acid; 6-APA | 551-16-6 | C8H12N2O3S | 详情 | 详情 |
| (IV) | 40168 | (2R)-2-([[3-(methylsulfonyl)-2-oxo-1-imidazolidinyl]carbonyl]amino)-2-phenylethanoic acid | C13H15N3O6S | 详情 | 详情 | |
| (V) | 40170 | (2R)-2-amino-2-phenylethanoic acid | C8H9NO2 | 详情 | 详情 | |
| (VI) | 36228 | 2-imidazolidinone | 120-93-4 | C3H6N2O | 详情 | 详情 |
| (VII) | 13467 | Methanesulfonyl chloride;Mesyl chloride;Methylsulfonyl chloride;Methanesulfonic acid chloride;Methanesulfonyl chloride;Methanesulphonyl chloride | 124-63-0 | CH3ClO2S | 详情 | 详情 |
| (VIII) | 36229 | 1-(methylsulfonyl)-2-imidazolidinone | 41730-79-4 | C4H8N2O3S | 详情 | 详情 |