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

Description

BENZHYDRYL 6,6-DIHYDROPENICILLIC ACID 1-OXIDE[TAZOBACTAM INTERMEDIATE] is an intermediate compound in the synthesis of Tazobactam Sodium Salt-13C2,15N1, which is a labeled analogue of Tazobactam Sodium Salt (T010100). Tazobactam Sodium Salt is a β-Lactamase inhibitor, used in combination with β-lactam antibiotics to enhance their effectiveness.

Uses

Used in Pharmaceutical Industry:
BENZHYDRYL 6,6-DIHYDROPENICILLIC ACID 1-OXIDE[TAZOBACTAM INTERMEDIATE] is used as a key intermediate in the synthesis of Tazobactam Sodium Salt, a β-Lactamase inhibitor. It plays a crucial role in enhancing the effectiveness of β-lactam antibiotics by inhibiting the enzymes that break them down, allowing the antibiotics to work more efficiently against bacterial infections.

Upstream product

• 20097-86-3 6-chloropenicillanic acid 
• 551-16-6 6-aminopenicillanic acid 
• 74189-25-6 diphenylmethyl 6α-bromopenicillanate 
• 551-16-6 6-Aminopenicillanic Acid 
• 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 of tazobactam intermediate

The invention provides a method for preparing a tazobactam intermediate. The method comprises the following steps: (1) introducing an amino-protecting group on an amino group of 6-APA (amino penicillanic acid) and performing oxidization with an oxidant, so as to obtain a compound 1, wherein the amino-protecting group is Boc preferably; (2) performing an esterification reaction on the compound 1 and an alcoholic compound, so as to obtain a compound 2, wherein the alcoholic compound is diphenyl carbinol preferably; (3) removing a Boc-NH-group from the compound 2, so as to obtain the tazobactam intermediate. According to the method, the amino group of 6-APA is protected by adopting protecting groups such as the Boc, so that a generated amino-protecting product is poor in water solubility andsteady in chemical properties; in addition, concentration is not needed in the first step, an oxidation reaction in the next step can be directly performed, and the total yield of the two steps reaches 80%.

Preparation method of 6-chloropenicillin sulfoxide diphenylmethyl ester and application thereof

The invention provides a preparation method of 6-chloropenicillin sulfoxide diphenylmethyl ester and application thereof. The preparation method comprises the following steps that in mixed liquid of hydrochloric acid and alcohol, 6-APA and sodium nitrite