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【结 构 式】 
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【分子编号】31959 【品名】(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 【CA登记号】 |
【 分 子 式 】C13H15BrN2O7S 【 分 子 量 】423.24138 【元素组成】C 36.89% H 3.57% Br 18.88% N 6.62% O 26.46% S 7.58% |
合成路线1
该中间体在本合成路线中的序号：(I)The reaction of 7-beta-bromoacetamido-7-alphamethoxycephalosporanic acid (I) with D-cysteine (II) in water at pH 7 gives 7-(2-aminocarboxyethylthio)acetamido-7-alpha-methoxycephalosporanic acid (III), which is then condensed with 5-mercapto-1-methyl-1H-tetrazole (IV) in water at pH 6.5-7 and at 60 C.
| 【1】 Iwamatsu, K.; Inoue, S.; Miyauchi, K.; Kondo, S.; Seki, S.; Yamada, Y. (Meiji Seika Kaisha, Ltd.); 7alpha-Methoxycephalosporin derivatives. JP 55083791 . |
| 【2】 Blancafort, P.; Castaner, J.; Loren, J.G.; Serradell, M.N.; MT-141. Drugs Fut 1982, 7, 6, 395. |
| 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) | 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 | |
| (II) | 25404 | D-cysteine; (S)-2-Amino-3-mercaptopropionic acid | 921-01-7 | C3H7NO2S | 详情 | 详情 |
| (III) | 31960 | (6R,7S)-3-[(acetoxy)methyl]-7-[(2-[[(2S)-2-amino-2-carboxyethyl]sulfanyl]acetyl)amino]-7-methoxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; 7-(2-aminocarboxyethyIthio)acetamido-7-alpha-methoxycephalosporanic acid | C16H21N3O9S2 | 详情 | 详情 | |
| (IV) | 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 |
合成路线2
该中间体在本合成路线中的序号：(II)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.
| 【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 |