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【结 构 式】 
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【药物名称】MG-2394 【化学名称】5,7-Dichloro-1-benzothien-2-ylsulfonamidomethylphosphonic acid 4-nitrophenyl monoester 【CA登记号】318461-32-4 【 分 子 式 】C15H11Cl2N2O7PS2 【 分 子 量 】497.27192 |
【开发单位】MethylGene (Originator) 【药理作用】Antibiotics, ANTIINFECTIVE THERAPY, beta-Lactam Enhancers, beta-Lactamase Inhibitors |
合成路线1
Addition of formaldehyde to 5,7-dichlorobenzothiophene-2-sulfonamide (I), followed by condensation with trimethyl phosphite, furnished the dimethyl (sulfonamidomethyl) phosphonate (II). The phosphonate ester function of (II) was then hydrolyzed by means of bromotrimethylsilane, producing phosphonic acid (III). This was finally coupled to 4-nitrophenol (IV) using trichloroacetonitrile in hot pyridine to afford the title mono-phosphonate ester.
| 【1】 Delorme, D.; Besterman, J.M.; Rahil, J. (MethylGene Inc.); Sulfonamidomethyl phosphonate inhibitors of beta-lactamase. EP 1194436; WO 0102411 . |
| 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) | 54795 | 5,7-dichloro-1-benzothiophene-2-sulfonamide | C8H5Cl2NO2S2 | 详情 | 详情 | |
| (II) | 54796 | dimethyl {[(5,7-dichloro-1-benzothiophen-2-yl)sulfonyl]amino}methylphosphonate | C11H12Cl2NO5PS2 | 详情 | 详情 | |
| (III) | 54797 | {[(5,7-dichloro-1-benzothiophen-2-yl)sulfonyl]amino}methylphosphonic acid | C9H8Cl2NO5PS2 | 详情 | 详情 | |
| (IV) | 11236 | 4-Nitrophenol; p-Nitrophenol | 100-02-7 | C6H5NO3 | 详情 | 详情 |
Extended Information