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【结 构 式】 
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【分子编号】11758 【品名】2-(5-Amino-1,2,4-thiadiazol-3-yl)-2-(methoxyimino)acetyl chloride 【CA登记号】 |
【 分 子 式 】C5H5ClN4O2S 【 分 子 量 】220.63916 【元素组成】C 27.22% H 2.28% Cl 16.07% N 25.39% O 14.5% S 14.53% |
合成路线1
该中间体在本合成路线中的序号：(IV)A new synthesis for [14C]-E-1040 has been described: The cyclization of [14C]-labeled potassium thiocyanate (I) with 2-(N-chlorocarboxamidino)-2-(methoxyimino)acetic acid (II) in methanol by means of triethylamine gives 2-(2-aminothiazol-4-yl)-2(Z)-(methoxyimino)acetic acid (III), which is treated with PCl5 in dichloromethane, yielding the corresponding acyl chloride (IV). Finally, this compound is condensed with 7-amino-3-(4-carbamoylquinuclidinio-1-ylmethyl)-3-cephem-4-carboxylate (V) by means of sodium acetate in dichloromethane.
| 【1】 Sugiyama, I.; Nomoto, S.; Mizuo, H.; Yamauchi, H.; Synthesis of (6R,7R)-7-[2-(5-amino-1,2,4-[5-C-14]thiadiazol-3-yl)-(Z)-2-methoxyiminoacetamido]-3-[(4-carbomoyl-1-quinuclidinio)methyl]ceph-3-em-4-carboxylate([C-14]E1040). J Label Compd Radiopharm 1991, 29, 12, 1309. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (II) | 11756 | 3-Amino-3-(chloroimino)-2-(methoxyimino)propionic acid | C4H6ClN3O3 | 详情 | 详情 | |
| (III) | 11757 | 2-(5-Amino-1,2,4-thiadiazol-3-yl)-2-(methoxyimino)acetic acid | C5H6N4O3S | 详情 | 详情 | |
| (III) | 45072 | 2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(methoxyimino)acetic acid | C5H6N4O3S | 详情 | 详情 | |
| (IV) | 11758 | 2-(5-Amino-1,2,4-thiadiazol-3-yl)-2-(methoxyimino)acetyl chloride | C5H5ClN4O2S | 详情 | 详情 | |
| (IV) | 45073 | 2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(methoxyimino)acetyl chloride | C5H5ClN4O2S | 详情 | 详情 | |
| (V) | 11759 | (6R,7R)-7-amino-3-[[4-(aminocarbonyl)-1-azoniabicyclo[2.2.2]oct-1-yl]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate | C16H22N4O4S | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(II)Alternatively, the title compound can be prepared by acylation of the imidazopyridazinium cephem derivative (IX) with acid chloride (II) in the presence of NaOAc.
| 【1】 Hamamura, K.; Shinohara, H.; Kodama, M.; Kuroda, H. (Eisai Co., Ltd.); Process for the production of cephem cpds.. EP 0832893 . |