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【结 构 式】 
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【分子编号】39964 【品名】(6R,7R)-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】 |
【 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% |
合成路线1
该中间体在本合成路线中的序号：(V)The protection of the amino group of ethyl 2-(2-amino-4-thiazolyl)-2-methoxyiminoacetate (I) with trityl chloride (B) by means of triethylamine in CH2Cl2 gives ethyl 2-(2-tritylamino-4-thiazolyl)-2-methoxyimino acetate (II), which is hydrolyzed to the corresponding acid (III) with NaOH in refluxing dioxane-water. The condensation of (III) with 7-aminocephalosporanic acid (IV) by means of dicyclohexylcarbodiimide in CH2Cl2 containing triethylamine affords 7-(2-(2-tritylamino-4-thiazolyl)-2-methoxyiminoacetamido]cephalosporanic acid (V). The elimination of the trityl group is performed with hot 55% formic acid yielding the corresponding free acid, which is finally treated with NaHCO3 in water.
| 【1】 Neuman, M.; Castaner, J.; HR-756. Drugs Fut 1978, 3, 10, 749. |
| 【2】 Heymes, R.; Lutz, A. (Aventis Pharma SA); Oxime derivatives of 7-aminothiazolylacetamidocephalosporanic acid processes for preparing them and pharmaceutical compositions incorporating them. BE 0850662; ES 455089; ES 466539; GB 1580621; GB 1580623; JP 52102293; JP 5247013 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (A) | 10180 | Thiourea | 62-56-6 | CH4N2S | 详情 | 详情 |
| (B) | 28630 | Triphenylchloromethane; 1-[Chloro(diphenyl)methyl]benzene; Trityl chloride | 76-83-5 | C19H15Cl | 详情 | 详情 |
| (I) | 10182 | Ethyl 2-(2-aminothiazole-4-yl)-2-methoxyiminoacetate; ethyl 2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetate; 2-(2-Amino-4-thiazolyl)-2-methoxyiminoacetic acid ethyl ester | 64485-88-7 | C8H11N3O3S | 详情 | 详情 |
| (II) | 39963 | ethyl 2-(methoxyimino)-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetate | C27H25N3O3S | 详情 | 详情 | |
| (III) | 25058 | 2-(methoxyimino)-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetic acid | 64485-90-1 | C25H21N3O3S | 详情 | 详情 |
| (IV) | 22747 | (6R,7R)-3-[(acetoxy)methyl]-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid | C10H12N2O5S | 详情 | 详情 | |
| (V) | 39964 | (6R,7R)-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 | C35H31N5O7S2 | 详情 | 详情 | |
| (VI) | 39961 | ethyl 4-chloro-2-(hydroxyimino)-3-oxobutanoate；(Z)-ethyl 4-chloro-2-(hydroxyimino)-3-oxobutanoate | C6H8ClNO4 | 详情 | 详情 | |
| (VII) | 39962 | ethyl 4-chloro-2-(methoxyimino)-3-oxobutanoate | C7H10ClNO4 | 详情 | 详情 | |
| (VIII) | 20853 | ethyl 2-(hydroxyimino)-3-oxobutanoate；(Z)-ethyl 2-(hydroxyimino)-3-oxobutanoate | C6H9NO4 | 详情 | 详情 | |
| (IX) | 20854 | ethyl 2-(methoxyimino)-3-oxobutanoate | C7H11NO4 | 详情 | 详情 | |
| (X) | 10181 | ethyl 4-bromo-2-(methoxyimino)-3-oxobutanoate | 60845-87-6 | C7H10BrNO4 | 详情 | 详情 |