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【结 构 式】 
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【分子编号】58729 【品名】disodium 3-({[((Z)-1-[2-(formylamino)-1,3-thiazol-4-yl]-2-{[(2R,3S)-2-methyl-4-oxo-1-sulfonatoazetidinyl]amino}-2-oxoethylidene)amino]oxy}methyl)-6,7-dihydroxy-2-quinoxalinecarboxylate 【CA登记号】 |
【 分 子 式 】C20H15N7Na2O11S2 【 分 子 量 】639.491216 【元素组成】C 37.56% H 2.36% N 15.33% Na 7.19% O 27.52% S 10.03% |
合成路线1
该中间体在本合成路线中的序号：(XIV)2-Formamido-4-thiazolecarboxylic acid (X) was activated as the mixed anhydride (XI) upon treatment with pivaloyl chloride and triethylamine. Subsequent coupling of anhydride (XI) with the aminoazetidinesulfonic acid (XII) provided the corresponding amide, which was further converted to the tetrabutylammonium sulfamate salt (XIII). The condensation between the keto group of (XIII) and hydroxylamine (IX) gave rise to the corresponding oxime (XIV). Finally, acid hydrolysis of the N-formyl group of (XIV) furnished the title compound.
| 【1】 Koster, W.H.; Sundeen, J.E.; Straub, H.; Ermann, P.H.; Treuner, U. (Bristol-Myers Squibb Co.); Heteroaroyl derivs. of monocyclic beta-lactam antibiotics. EP 0484881; JP 1992283579 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (IX) | 58725 | 3-[(aminooxy)methyl]-6,7-dihydroxy-2-quinoxalinecarboxylic acid | C10H9N3O5 | 详情 | 详情 | |
| (X) | 31132 | 2-[2-(formylamino)-1,3-thiazol-4-yl]-2-oxoacetic acid | C6H4N2O4S | 详情 | 详情 | |
| (XI) | 58726 | 1,1-dimethylpropanoic [2-(formylamino)-1,3-thiazol-4-yl](oxo)acetic anhydride | C11H12N2O5S | 详情 | 详情 | |
| (XII) | 58727 | (2R,3S)-3-amino-2-methyl-4-oxo-1-azetidinesulfonic acid | C4H8N2O4S | 详情 | 详情 | |
| (XIII) | 58728 | N,N,N-tributyl-1-butanaminium (2R,3S)-3-({2-[2-(formylamino)-1,3-thiazol-4-yl]-2-oxoacetyl}amino)-2-methyl-4-oxo-1-azetidinesulfonate | C26H45N5O7S2 | 详情 | 详情 | |
| (XIV) | 58729 | disodium 3-({[((Z)-1-[2-(formylamino)-1,3-thiazol-4-yl]-2-{[(2R,3S)-2-methyl-4-oxo-1-sulfonatoazetidinyl]amino}-2-oxoethylidene)amino]oxy}methyl)-6,7-dihydroxy-2-quinoxalinecarboxylate | C20H15N7Na2O11S2 | 详情 | 详情 |