(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 -Drug Synthesis Database

【结构式】

【分子编号】33371

【品名】(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

【CA登记号】

【分子式】C₁₈H₁₈N₂O₇S

【分子量】406.4162

【元素组成】C 53.2% H 4.46% N 6.89% O 27.56% S 7.89%

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：(XII)

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.

参考文献中间体

合成目标

【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	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