87579-78-0

Basic information

• Product Name: BENZHYDRYL 6,6-DIHYDROPENICILLIC ACID 1-OXIDE[TAZOBACTAM INTERMEDIATE]
• Synonyms: BENZHYDRYL 6,6-DIHYDROPENICILLIC ACID 1-OXIDE[TAZOBACTAM INTERMEDIATE];(2S,5R)-3,3-Dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid diphenylmethyl ester 4-oxide;(2S,5R)-Benzhydryl 3,3-diMethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate 4-oxide;(2S,5R)-3,3-dimethyl-7-oxo-4- oxide-4-Thia-1-azabicyclo[3.2. 0]heptane-2-carboxylic Acid Diphenylmethyl Ester
• CAS NO: 87579-78-0
• Molecular Formula: C₂₁H₂₁NO₄S
• Molecular Weight: 383.46074
• Mol File: 87579-78-0.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 598.7±50.0 °C(Predicted)
• Appearance: Yellow Solid
• Density: 1.37
• Storage Temp.: 2-8°C
• Solubility: Dichloromethane
• PKA: -3.44±0.60(Predicted)
• CAS DataBase Reference: BENZHYDRYL 6,6-DIHYDROPENICILLIC ACID 1-OXIDE[TAZOBACTAM INTERMEDIATE](CAS DataBase Reference)
• NIST Chemistry Reference: BENZHYDRYL 6,6-DIHYDROPENICILLIC ACID 1-OXIDE[TAZOBACTAM INTERMEDIATE](87579-78-0)
• EPA Substance Registry System: BENZHYDRYL 6,6-DIHYDROPENICILLIC ACID 1-OXIDE[TAZOBACTAM INTERMEDIATE](87579-78-0)

Safety Data

• Hazardous Substances Data: 87579-78-0(Hazardous Substances Data)

Usage

Uses

(2S,5R)-3,3-dimethyl-7-oxo-4-oxide-4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid Diphenylmethyl Ester is an intermediate in the synthesis of Tazobactam Sodium Salt-13C2,15N1, which is the labelled analogue of Tazobactam Sodium Salt (T010100), which is a β-Lactamase inhibitor, used with β-lactam antibiotics to enhance their effect.

Upstream product

• 551-16-6 6-Aminopenicillanic Acid 
• 20097-86-3 6-chloropenicillanic acid 
• 551-16-6 6-aminopenicillanic acid 
• 74189-25-6 diphenylmethyl 6α-bromopenicillanate 
• 24138-28-1 6-bromopenicillanic acid 
• 80353-26-0 6α-bromopenicillan-3α-carboxylic acid diphenylmethyl ester-1β-oxide 

Downstream Products

• 85573-73-5 2β-(chloro)methyl-2α-methyl-6,6-dihydropenam-3α-carboxylic acid benzhydryl ester 
• 89786-04-9 tazobactam acid 
• 89789-07-1 (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 
• 1026477-53-1 (2S,3R,5R)-3-Chlorocarbonyl-3-methyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester 
• 182750-64-7 benzhydryl 2β-(chloroacetoxy)methyl-1,1-dioxo-penicillanate 
• 182750-66-9 (2S,3R,5R)-3-Methyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2,3-dicarboxylic acid 2-benzhydryl ester 
• 182750-65-8 benzhydryl 2β-hydroxymethyl-1,1-dioxopenicillanate 
• 188249-92-5 diphenylmethyl (2S,3R,5R)-3-formyl-3-methyl-4,4,7-trioxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylate 
• 87579-79-1 (R)-benzhydryl 2-((R)-2-(benzo[d]thiazol-2-yldisulfanyl)-4-oxoazetidin-1-yl)-3-methylbut-3-enoate 
• 89786-04-9 tazobactam 
• 122661-93-2 2α-methyl-2β-[(1,2,3-triazol-1-yl)methyl]penicillin-3α-carboxylic acid diphenylmethyl ester 
• 85573-72-4 (R)-2-[2-(benzothiazol-2-yldisulfanyl)-4-oxo-azetidin-1-yl]-3-methyl-butyl-3-enoic acid benzhydryl ester 

Relevant articles and documents

Application of Continuous Flow in Tazobactam Synthesis

Tazobactam is a β-lactamase inhibitor. In this work, a combination of continuous flow and batch experiments for the synthesis of tazobactam has been developed. The first three steps and the preparation of the peroxyacetic acid are continuously carried out in the microreactors, which improves the procedure safety and efficiency. There is also a final step of the deprotection reaction in the microreactor, which can increase the yield and reduce the formation of impurities. Under optimized process conditions, the total yield of the target product reached 37.09% (30.93% in batch). The continuous flow method not only greatly reduces the reaction time but also significantly improves procedure safety and increases the yield.

Preparation method for tazobactam intermediate

The invention discloses a preparation method for a tazobactam intermediate. The method comprises the following steps of: under the action of peracetic acid, enabling 6-APA to react with diphenyl hydrazone to generate a compound 4; under the action of sulf

Preparation method of benzhydryl s-oxopenicillanate

The invention discloses a preparation method of benzhydryl s-oxopenicillanate. The compound is prepared through an oxidation and esterification one-pot reaction and a reduction reaction by using 6-bromo-penicillanic acid as an initial raw material. A redu