3-hydroxy-5-sulfanyl-4-isothiazolecarboxylic acid -Drug Synthesis Database

【结构式】

【分子编号】32288

【品名】3-hydroxy-5-sulfanyl-4-isothiazolecarboxylic acid

【CA登记号】

【分子式】C₄H₃NO₃S₂

【分子量】177.20476

【元素组成】C 27.11% H 1.71% N 7.9% O 27.09% S 36.19%

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：(I)

The condensation of 4-carboxy-3-hydroxy-5-mercaptoisothiazol (I) with 7beta-bromoacetamido-7alpha-methoxycephalosporanic acid (II) gives 7beta-(4-carboxy-3-hydroxyisothiazol-5-yl)thioacetamido-7alpha-methoxycephalosporanic acid (III), which by treatment with NaHCO3 in hot water is converted into 7beta-[4-(carbamoyl)(carboxy)methylene-1,3-dithietan-2-yl]carboxamido-7alpha-methoxycephalosporanic acid (IV). Finally, this compound is condensed with 5-mercapto-1-methyltetrazol (V) by means of Na2CO3 in water.

参考文献中间体

合成目标

【1】 Iwanami, M.; Maeda, T.; Nagano, Y.; Fujimoto, M.; Nagano, N.; Yamazaki, A.; 7alpha-Methoxy-7beta-(1,3-dithietane-2-carboxamido)cephalosporanic acid derivatives. BE 0867994; DE 2824559; FR 2405952; NL 7806208; US 4263432; US 4404373 .
【2】 Blancafort, P.; Castaner, J.; Sweetman, A.J.; Serradell, M.N.; Cefotetan. Drugs Fut 1981, 6, 10, 609.

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)	32288	3-hydroxy-5-sulfanyl-4-isothiazolecarboxylic acid		C₄H₃NO₃S₂	详情	详情
(II)	31959	(6R,7S)-3-[(acetoxy)methyl]-7-[(2-bromoacetyl)amino]-7-methoxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; 7-beta-bromoacetamido-7-alphamethoxycephalosporanic acid		C₁₃H₁₅BrN₂O₇S	详情	详情
(III)	32289	(6R,7S)-3-[(acetoxy)methyl]-7-([2-[(4-carboxy-3-hydroxy-5-isothiazolyl)sulfanyl]acetyl]amino)-7-methoxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid		C₁₇H₁₇N₃O₁₀S₃	详情	详情
(IV)	32290	(6R,7S)-3-[(acetoxy)methyl]-7-([[4-(2-amino-1-carboxy-2-oxoethylidene)-1,3-dithietan-2-yl]carbonyl]amino)-7-methoxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid		C₁₇H₁₇N₃O₁₀S₃	详情	详情
(V)	28420	5-Mercapto-1-methyl-1H-tetrazole; 1-Methyl-1H-1,2,3,4-tetraazol-5-ylhydrosulfide	13183-79-4	C₂H₄N₄S	详情	详情

Extended Information