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【结 构 式】 
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【药物名称】Oximonam sodium, SQ-82629, SQ-82291 【化学名称】[[(2S,3S)-3-[(2-Amino-4-thiazolyl)glyoxylamido]-2-methyl-4-oxo-1-azetidinyl]oxy]acetic acid 3(2)-(Z)-(O)-methyloxime sodium salt 【CA登记号】90849-08-4, 90898-90-1 (free acid) 【 分 子 式 】C12H14N5NaO6S 【 分 子 量 】379.32908 |
【开发单位】Bristol-Myers Squibb (Originator) 【药理作用】Monobactams |
合成路线1
The condensation of 3-(tert butoxycarbonyl amino)-1-hydroxy-4-methylazetidin-2-one (I) with chloroacetic acid (II) by means of K2CO3 gives 2-(3-(tert butoxycarbonylamino)-4-methyl-2-oxoazetidin-1-yloxy]acetic acid (III), which is deprotected with trifluoroacetic acid yielding 2-(3-amino 4-methyl-2-oxoazetidin-1-yloxy)acetic acid (IV). Finally, this compound is condensed with 2-(2-amino-thiazol-4-yl)-2-(methoxyimino)acetyl chloride (V) by means of Na2CO3.
| 【1】 Breuer, H.; et al.; [(2-Oxo-1-azetidinyl)oxy]acetic acids: A new class of synthetic monobactams. J Antibiot 1985, 38, 6, 813. |
| 【2】 Miller, M.J.; Woulfe, S.R.; Synthesis and biological activity of substituted [(3(S)-(acylamino)-2-oxo-1-azetidinyl]oxy]acetic acids. A new class of heteroatom-activated beta-lactam antibiotics. J Med Chem 1985, 28, 10, 1447. |
| 【3】 Breuer, H.; Straub, H.; Treuner, U.D. (Von Heyden); beta-Lactam derivs.. DE 3328047; GB 2125794 . |
| 【4】 Castaner, J.; Prous, J.; Oximonam sodium. Drugs Fut 1986, 11, 9, 759. |
| 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) | 24312 | butyl (2S,3S)-1-hydroxy-2-methyl-4-oxoazetidinylcarbamate | C9H16N2O4 | 详情 | 详情 | |
| (II) | 11847 | 2-Chloroacetic acid; Chloroacetic Acid | 79-11-8 | C2H3ClO2 | 详情 | 详情 |
| (III) | 24314 | 2-([(2S,3S)-3-[(butoxycarbonyl)amino]-2-methyl-4-oxoazetidinyl]oxy)acetic acid | C11H18N2O6 | 详情 | 详情 | |
| (IV) | 24315 | 2-[[(2S,3S)-3-amino-2-methyl-4-oxoazetidinyl]oxy]acetic acid | C6H10N2O4 | 详情 | 详情 | |
| (V) | 24316 | 2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl chloride | C6H6ClN3O2S | 详情 | 详情 |