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【结 构 式】 
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【分子编号】33373 【品名】(1R)-2-chloro-2-oxo-1-phenylethyl 2,2-dichloroacetate 【CA登记号】 |
【 分 子 式 】C10H7Cl3O3 【 分 子 量 】281.52188 【元素组成】C 42.66% H 2.51% Cl 37.78% O 17.05% |
合成路线1
该中间体在本合成路线中的序号：(A)a) By reaction of 1-sulfamoylmethyltetrazol-5-thiol (IX) with 7-mandelamidocephalosporanic acid (XII) by means of NaHCO3. b) ByCondensation of 1-sulfamoylmethyltetrazol-5-thiol (IX) with 7-aminocephalosporanic acid (X) by means of NaHCO3 in acetone - water to give 7-amino-3-(1-sulfamoyl-methyltetrazol-5-ylthio-methyl)-3-cephem-4-carboxylic acid (XI). Finally, this compound is acylated with D-O-dichloroacetylmandeloyl chloride (A) by means of NaHCO3 in acetone-water to afford the target compound. b) ByCondensation of 1-sulfamoylmethyltetrazol-5-thiol (IX) with 7-aminocephalosporanic acid (X) by means of NaHCO3 in acetone - water to give 7-amino-3-(1-sulfamoyl-methyltetrazol-5-ylthio-methyl)-3-cephem-4-carboxylic acid (XI). Finally, this compound is acylated with D-O-dichloroacetylmandeloyl chloride (A) by means of NaHCO3 in acetone-water to afford the target compound.
| 【1】 Berges, D.A.; 7-Acyl-3-(sulfonic acid and sulfamoyl substituted tetrazolyl thiomethyl)cephalosporins.. DE 2611270; FR 2304343; US 4048311 . |
| 【2】 Castaner, J.; Serradell, M.N.; Thorpe, P.; Blancafort, P.; Cefonicid sodium. Drugs Fut 1979, 4, 9, 634. |
| 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) | 33373 | (1R)-2-chloro-2-oxo-1-phenylethyl 2,2-dichloroacetate | C10H7Cl3O3 | 详情 | 详情 | |
| (IX) | 33370 | (5-sulfanyl-1H-1,2,3,4-tetraazol-1-yl)methanesulfonic acid | C2H4N4O3S2 | 详情 | 详情 | |
| (X) | 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 | |
| (XI) | 33372 | (6R,7R)-7-amino-8-oxo-3-([[1-(sulfomethyl)-1H-1,2,3,4-tetraazol-5-yl]sulfanyl]methyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid | C10H12N6O6S3 | 详情 | 详情 | |
| (XII) | 33371 | (6R,7R)-3-[(acetoxy)methyl]-7-[[(2R)-2-hydroxy-2-phenylethanoyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid | C18H18N2O7S | 详情 | 详情 |