3-[(acetoxy)methyl]-7-([2-(methoxyimino)-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetyl]amino)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid -Drug Synthesis Database

【结构式】

【分子编号】30338

【品名】3-[(acetoxy)methyl]-7-([2-(methoxyimino)-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetyl]amino)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

【CA登记号】66254-46-4

【分子式】C₃₅H₃₁N₅O₇S₂

【分子量】697.79264

【元素组成】C 60.24% H 4.48% N 10.04% O 16.05% S 9.19%

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：(III)

The condensation of 2-(methoxyimino)-2-(2-tritylaminothiazol-4-yl)acetic acid (I) with 7-aminocephalosporanic acid (II) by means of dicyclohexylcarbodiimide in CH2Cl2 gives 7-[2-(methoxyimino)-2-(2-tritylaminothiazol-4-yl)acetamido]cephalosporanic acid (III), which is deprotected by means of formic acid in water yielding 7-[2-(methoxyimino)-2-(2-aminothiazol-4-yl)acetamido]cephalosporanic acid (IV). Finally, this compound is condensed with 5-(carboxymethyl)-2-mercapto-4-methyl-1,3-thiazole (V) by means of NaHCO3 or NaOH in hot water.

参考文献中间体

合成目标

【1】 Wolff, S.; et al.; Results of a multicenter phase III trial of magnetic resonance angiography (MRA) with MS-325 for the detection of peripheral vascular disease in the aortolliac region. Circulation 2002, 106, 19, Suppl. 2, Abst 3408.
【2】 Duerckeimer, W.; et al. (Aventis Pharma AG); Cephem derivative. BE 0865632; FR 2385722; GB 1604971; JP 5706887; US 4278793 .
【3】 Serradell, M.N.; Castaner, J.; Cefodizime. Drugs Fut 1984, 9, 3, 177.

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)	25058	2-(methoxyimino)-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetic acid	64485-90-1	C₂₅H₂₁N₃O₃S	详情	详情
(II)	15672	7-Aminocephalosporanic acid; 3-[(acetoxy)methyl]-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; 7-ACA		C₁₀H₁₂N₂O₅S	详情	详情
(III)	30338	3-[(acetoxy)methyl]-7-([2-(methoxyimino)-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetyl]amino)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid	66254-46-4	C₃₅H₃₁N₅O₇S₂	详情	详情
(IV)	30339	3-[(acetoxy)methyl]-7-[[2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid		C₁₆H₁₇N₅O₇S₂	详情	详情
(V)	19846	2-(4-methyl-2-sulfanyl-1,3-thiazol-5-yl)acetic acid	34272-64-5	C₆H₇NO₂S₂	详情	详情

Extended Information