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【结 构 式】

【分子编号】33372

【品名】(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

【CA登记号】

【 分 子 式 】C10H12N6O6S3

【 分 子 量 】408.44012

【元素组成】C 29.41% H 2.96% N 20.58% O 23.5% S 23.55%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(XI)

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
Extended Information