2-[[(2S,3S)-3-amino-2-methyl-4-oxoazetidinyl]oxy]acetic acid -Drug Synthesis Database

【结构式】

【分子编号】24315

【品名】2-[[(2S,3S)-3-amino-2-methyl-4-oxoazetidinyl]oxy]acetic acid

【CA登记号】

【分子式】C₆H₁₀N₂O₄

【分子量】174.15648

【元素组成】C 41.38% H 5.79% N 16.09% O 36.75%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号：(IV)

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.

参考文献中间体

合成目标

【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

Extended Information