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Oximonam sodium, SQ-82629, SQ-82291

肟莫南 Chemical Name: [[(2S,3S)-3-[(2-Amino-4-thiazolyl)glyoxylamido]-2-methyl-4-oxo-1-azetidinyl]oxy]acetic acid 3(2)-(Z)-(O)-methyloxime sodium salt; [[4(S)-Methyl-3(S)-[(2-amino-4-thiazolyl)-2(Z)-(methoxyimino)acetamido]-2-oxo-1-azetidinyl]oxy]acetic acid sodium salt
CAS No. 90849-08-4, 90898-90-1 (free acid)
项目整合开发状态: Biological Testing
项目研究机构: Bristol-Myers Squibb (Originator)
合成路线: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.
📌 参考资料/链接:
参考文献标题:beta-Lactam derivs.
文献作者:Breuer,H.; Straub,H.; Treuner,U.D.(Von Heyden)
参考来源:DE 3328047; GB 2125794

📄 详细内容


合成路线: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.

参考文献标题:Oximonam sodium
文献作者:Castar,J.; Prous,J.
参考来源:Drugs Fut 1986,11(9),759


合成路线: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.

参考文献标题: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
文献作者:Woulfe,S.R.; Miller,M.J.
参考来源:J Med Chem 1985,28(10),1447


合成路线: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.
参考文献标题:[(2-Oxo-1-azetidinyl)oxy]acetic acids: A new class of synthetic monobactams
文献作者:Breuer,H.; Straub,H.; Treuner,U.D.; Drossard,J.M.; Hohn,H.; Lindner,K.R.
参考来源:J Antibiot 1985,38(6),813


产品链接: CAS No. 90849-08-4››

产品链接: CAS No.90898-90-1››