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【结 构 式】 
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【药物名称】PNU-176968 【化学名称】N-[3-[3-Fluoro-4-(5-thiazolyl)phenyl]-2-oxooxazolidin-5(S)-ylmethyl]acetamide 【CA登记号】 【 分 子 式 】C15H14FN3O3S 【 分 子 量 】335.35953 |
【开发单位】Pfizer (Originator) 【药理作用】Antibacterial Drugs, ANTIINFECTIVE THERAPY, Oxazolidinones |
合成路线1
Lithiation of thiazole (I) with butyllithium at -78 C, followed by quenching with chlorotrimethylsilane afforded 2-(trimethylsilyl)thiazole (II). A second lithiation generated the 5-lithio thiazole, which was converted to the stannyl derivative (III) upon reaction with tributylstannyl chloride. Then, palladium-catalyzed coupling of (III) with the iodophenyl oxazolidine (IV) in refluxing dioxan furnished the title compound.
| 【1】 Anderson, D.J.; Allwine, D.A.; Genin, M.J.; et al.; Carbon-carbon-linked 5-membered heteroarylphenyl oxazolidinones with broad-spectrum antibacterial activity. 39th Intersci Conf Antimicrob Agents Chemother (Sept 26 1999, San Francisco) 1999, Abst F570. |
| 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) | 23000 | 1,3-thiazole | 288-47-1 | C3H3NS | 详情 | 详情 |
| (II) | 10720 | 2-(Trimethylsilyl)-1,3-thiazole | 79265-30-8 | C6H11NSSi | 详情 | 详情 |
| (III) | 38137 | 5-(tributylstannyl)-2-(trimethylsilyl)-1,3-thiazole | C18H37NSSiSn | 详情 | 详情 | |
| (IV) | 38138 | N-[[(5S)-3-(3-fluoro-4-iodophenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide | C12H12FIN2O3 | 详情 | 详情 |
Extended Information