CAS: 85573-73-5; 2β-(Chloro)Methyl-2α-Methyl-6,6-Dihydropenam-3α-Carboxylic Acid Benzhydryl Ester

英文名称2β-(Chloro)Methyl-2α-Methyl-6,6-Dihydropenam-3α-Carboxylic Acid Benzhydryl Ester
中文名称他唑巴坦氯化物
CAS编号85573-73-5
FDA UNII编号:N3FZV4ADG6
分子式:C21H20ClNO3S分子量:401.91
产品CID: 1852678
产品分类分析化学 → 标准品 → 药典标准品和杂质标准品

相似结构搜索
InChIKey: JCCKXLWAWRUWBK-LMNJBCLMSA-N
1S/C21H20ClNO3S/c1-21(13-22)19(23-16(24)12-17(23)27-21)20(25)26-18(14-8-4-2-5-9-14)15-10-6-3-7-11-15/h2-11,17-19H,12-13H2,1H3/t17-,19+,21+/m1/s1
计算化学: 氢键受体数4.0氢键供体数0.0可旋转键数6.0

物理性质

沸点565.1±50.0 °C(预测)
密度1.36±0.1 g/cm3(预测)
pKa:-3.84±0.60(预测)
PSA:71.91
LogP:3.9284
产品应用该化合物用于合成TAZOBACTAM SODIUM SALT-15N3(T010103)的一种中间体,这是一种Β-林丹抑制剂,与Β-乳性抗生素一起使用,以提高其效果.

MSDS等安全信息

上下游产品

(R)-2-[2-(benzothiazol-2-yldisulfanyl)-4-oxo-azetidin-1-yl]-3-methyl-butyl-3-enoic acid benzhydryl ester (R)-benzhydryl 2-((R)-2-(benzo[d]thiazol-2-yldisulfanyl)-4-oxoazetidin-1-yl)-3-methylbut-3-enoate 6-aminopenicillanic acid benzhydryl-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate-4-oxide (2S,3S,5R)-3-(4-methyl-iinidazol-1-ylmethyl)-3-methyl-4,4,7-trioxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester tazobactam acid (2S,3S,5R) 3-methyl-7-oxo-3-(1H-1,2,3-triazol-1-yl-methyl)-4-thia-1-azabicyclo[3.2.0]heptane2-carboxylic acid 4,4-dioxide, diphenyl methyl ester

合成工艺路线路线简述

87579-79-1 = 85573-73-5
反应条件:1.1 Reagents: Sulfuryl Chloride Solvents: Dichloromethane
标题:Improved Process For The Synthesis Of Benzhydryl 2β-Chloromethylpenicillanate
作者:Chen,Wan-Cheng; Et Al
参考文献:Shanxi Daxue Xuebao 日期:2001 卷标:24(4) 页码:329-330]

123285-28-9 + 149-30-4 = 85573-73-5
反应条件:1.1 Solvents: Toluene; 4 H,Reflux2.1 Reagents: Sodium Nitrite,Hydrochloric Acid Solvents: Water; Rt -> 5 °C; 2 H,0 - 5 °C
标题:New Method For Synthesis Of Tazobactam
作者:Hu,Yue-Hua; Et Al
参考文献:Anhui Shifan Daxue Xuebao 日期:2003 卷标:26(1) 页码:48-50]

123285-28-9 + 149-30-4 = 85573-73-5
反应条件:1.1 Solvents: Toluene2.1 Reagents: Sulfuryl Chloride Solvents: Dichloromethane
标题:Improved Process For The Synthesis Of Benzhydryl 2β-Chloromethylpenicillanate
作者:Chen,Wan-Cheng; Et Al
参考文献:Shanxi Daxue Xuebao 日期:2001 卷标:24(4) 页码:329-330]

123285-25-6 = 85573-73-5
反应条件:1.1 Reagents: Zinc,Ammonium Chloride Solvents: Water; 1 H,10 °C2.1 Solvents: Toluene; 4 H,Reflux3.1 Reagents: Sodium Nitrite,Hydrochloric Acid Solvents: Water; 2 H,0 - 5 °C
标题:New Process For The Synthesis Of Tazobactam. A β-Lactamase Inhibitor
作者:Hu,Yue-Hua; Et Al
参考文献:Hecheng Huaxue 日期:2003 卷标:11(3) 页码:243-245]

80353-26-0 = 85573-73-5
反应条件:1.1 Reagents: Ammonium Acetate Solvents: Tetrahydrofuran,Water; 0 °C1.2 Reagents: Zinc; 10 Min,0 °C; 3.5 H,0 °C2.1 Solvents: Toluene; 80 °C; 5 Min,80 °C -> Reflux; 90 Min,Reflux3.1 Reagents: Cupric Chloride Solvents: Dichloromethane; 4 H,Rt
标题:Synthesis Of Tazobactam,β-Lactamase Inhibitor
作者:Li,Yang; Et Al
参考文献:Transactions Of Tianjin University 日期:2002 卷标:8(1) 页码:33-36]

24138-28-1 + 5350-57-2 = 85573-73-5
反应条件:1.1 Reagents: Manganese Oxide (Mno2) Solvents: Methanol2.1 Reagents: Ammonium Acetate,Zinc Solvents: Tetrahydrofuran3.1 -4.1 Reagents: Sulfuryl Chloride Solvents: Dichloromethane
标题:Synthetic Process Of Tazobactam,A β-Lactamase Inhibitor
作者:Deng,Yong; Et Al
参考文献:Zhongguo Yaowu Huaxue Zazhi 日期:2001 卷标:11(2) 页码:93-95]

75527-84-3 = 85573-73-5
反应条件:1.1 Reagents: Formic Acid,Hydrogen Peroxide Solvents: Water; 30 Min,0 - 5 °C; 4 H2.1 Reagents: Zinc,Ammonium Chloride Solvents: Water; 1 H,10 °C3.1 Solvents: Toluene; 4 H,Reflux4.1 Reagents: Sodium Nitrite,Hydrochloric Acid Solvents: Water; 2 H,0 - 5 °C
标题:New Process For The Synthesis Of Tazobactam. A β-Lactamase Inhibitor
作者:Hu,Yue-Hua; Et Al
参考文献:Hecheng Huaxue 日期:2003 卷标:11(3) 页码:243-245]

87579-78-0 = 85573-73-5
反应条件:1.1 Reagents: 2-Mercaptobenzothiazole Solvents: Toluene; 3 H,Reflux1.2 Reagents: Sulfuryl Chloride Solvents: Dichloromethane; 0.5 H,-15 °C
标题:Synthesis Of Tazobactam
作者:Liu,Xiulan; Et Al
参考文献:Taiyuan Ligong Daxue Xuebao 日期:2002 卷标:33(6) 页码:663-665]

87579-79-1 = 85573-73-5
反应条件:1.1 Reagents: Sodium Nitrite,Hydrochloric Acid Solvents: Dichloromethane,Water
标题:A Facile Halogenative Cyclization Of 4-(2-Benzothiazolyldithio)Azetidinones (Kamiya'S Disulfide) Into 2β-(Halomethyl)Penams In A Two-Layer System
作者:Tanaka,Hideo; Et Al
参考文献:Bulletin Of The Chemical Society Of Japan 日期:1989 卷标:62(9) 页码:3046-8]

87579-79-1 = 85573-73-5
反应条件:1.1 Reagents: Cupric Chloride Solvents: Dichloromethane; 4 H,Rt
标题:Synthesis Of Tazobactam,β-Lactamase Inhibitor
作者:Li,Yang; Et Al
参考文献:Transactions Of Tianjin University 日期:2002 卷标:8(1) 页码:33-36]

100349-42-6 + 149-30-4 = 85573-73-5
反应条件:1.1 -2.1 Reagents: Sulfuryl Chloride Solvents: Dichloromethane
标题:Synthetic Process Of Tazobactam,A β-Lactamase Inhibitor
作者:Deng,Yong; Et Al
参考文献:Zhongguo Yaowu Huaxue Zazhi 日期:2001 卷标:11(2) 页码:93-95]

123285-28-9 + 149-30-4 = 85573-73-5
反应条件:1.1 Solvents: Toluene; 4 H,Reflux2.1 Reagents: Sodium Nitrite,Hydrochloric Acid Solvents: Water; 2 H,0 - 5 °C
标题:New Process For The Synthesis Of Tazobactam. A β-Lactamase Inhibitor
作者:Hu,Yue-Hua; Et Al
参考文献:Hecheng Huaxue 日期:2003 卷标:11(3) 页码:243-245]

100349-41-5 = 85573-73-5
反应条件:1.1 Reagents: Ammonium Acetate,Zinc Solvents: Tetrahydrofuran2.1 -3.1 Reagents: Sulfuryl Chloride Solvents: Dichloromethane
标题:Synthetic Process Of Tazobactam,A β-Lactamase Inhibitor
作者:Deng,Yong; Et Al
参考文献:Zhongguo Yaowu Huaxue Zazhi 日期:2001 卷标:11(2) 页码:93-95]

123285-25-6 = 85573-73-5
反应条件:1.1 Reagents: Zinc,Ammonium Chloride Solvents: Ethyl Acetate,Water; 1 H,10 °C; 30 Min,5 °C2.1 Solvents: Toluene; 4 H,Reflux3.1 Reagents: Sodium Nitrite,Hydrochloric Acid Solvents: Water; Rt -> 5 °C; 2 H,0 - 5 °C
标题:New Method For Synthesis Of Tazobactam
作者:Hu,Yue-Hua; Et Al
参考文献:Anhui Shifan Daxue Xuebao 日期:2003 卷标:26(1) 页码:48-50]

80353-26-0 = 85573-73-5
反应条件:1.1 Reagents: Acetic Acid,Zinc Solvents: Acetonitrile2.1 Solvents: Toluene3.1 Reagents: Cupric Chloride Solvents: Dichloromethane
标题:Synthesis Of 2β-Azidomethylpenicillin 1,1-Dioxides And 3β-Azido-3α-Methylcepham 1,1-Dioxides
作者:Micetich,Ronald G.; Et Al
参考文献:Synthesis 日期:1986 卷标:(4) 页码:292-6]

24138-28-1 + 5350-57-2 = 85573-73-5
反应条件:1.1 Solvents: Dichloromethane; 0 °C1.2 Reagents: Iodine Solvents: Dichloromethane1.3 Reagents: Alumina,Potassium Peroxymonosulfate Sulfate (2Khso5.Khso4.K2So4) Solvents: Water; 30 Min,0 °C; 3 H,0 °C2.1 Reagents: Ammonium Acetate Solvents: Tetrahydrofuran,Water; 0 °C2.2 Reagents: Zinc; 10 Min,0 °C; 3.5 H,0 °C3.1 Solvents: Toluene; 80 °C; 5 Min,80 °C -> Reflux; 90 Min,Reflux4.1 Reagents: Cupric Chloride Solvents: Dichloromethane; 4 H,Rt
标题:Synthesis Of Tazobactam,β-Lactamase Inhibitor
作者:Li,Yang; Et Al
参考文献:Transactions Of Tianjin University 日期:2002 卷标:8(1) 页码:33-36]

24138-28-1 + 5350-57-2 = 85573-73-5
反应条件:1.1 Reagents: Peracetic Acid Solvents: Chloroform,Water1.2 Reagents: Potassium Iodide1.3 Reagents: Peracetic Acid Solvents: Water1.4 Reagents: Sulfuric Acid Solvents: Water2.1 Reagents: Acetic Acid,Zinc Solvents: Acetonitrile3.1 Solvents: Toluene4.1 Reagents: Cupric Chloride Solvents: Dichloromethane
标题:Synthesis Of 2β-Azidomethylpenicillin 1,1-Dioxides And 3β-Azido-3α-Methylcepham 1,1-Dioxides
作者:Micetich,Ronald G.; Et Al
参考文献:Synthesis 日期:1986 卷标:(4) 页码:292-6]

75527-84-3 = 85573-73-5
反应条件:1.1 Reagents: Acetic Acid,Hydrogen Peroxide Solvents: Water; 30 Min; 4 H2.1 Reagents: Zinc,Ammonium Chloride Solvents: Ethyl Acetate,Water; 1 H,10 °C; 30 Min,5 °C3.1 Solvents: Toluene; 4 H,Reflux4.1 Reagents: Sodium Nitrite,Hydrochloric Acid Solvents: Water; Rt -> 5 °C; 2 H,0 - 5 °C
标题:New Method For Synthesis Of Tazobactam
作者:Hu,Yue-Hua; Et Al
参考文献:Anhui Shifan Daxue Xuebao 日期:2003 卷标:26(1) 页码:48-50

📜2-(2-Benzothiazolyldithio)-A-(1-Methylethenyl)-4-Oxo-1-Azetidineacetic Acid Diphenylmethyl Ester置于盐酸,Sodium Nitrite体系中,用二氯甲烷,水作为反应溶剂,化学反应生成他唑巴坦氯化物
参考文献:一种他唑巴坦酸,他唑巴坦二苯甲酯制备工艺与应用
标题:一种他唑巴坦酸,他唑巴坦二苯甲酯制备工艺与应用
摘要:本发明涉及到一种他唑巴坦二苯甲酯,他唑巴坦酸的制备工艺与应用,制备路径由甲苯,2‑巯基苯并噻唑和脱溴物作为起始物经过开环反应,氯化反应,缩合反应,双氧化反应后制备得到他唑巴坦二苯甲酯,再经过脱保护反应之后将他唑巴坦二苯甲酯转换成他唑巴坦酸;而本方案中的制备方式在现有技术的碘代反应的基础上做出改进,引进氯代反应,优化反应质量,提高产品纯度,降低反应过程中有毒有害,易燃易爆物质的使用,使反应更加绿色,环保;且产物产率可高达98%‑99.92%,制备成本也低于现有技术中的制备工艺.