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

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

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

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

Downstream Products

• 85573-72-4 (R)-2-[2-(benzothiazol-2-yldisulfanyl)-4-oxo-azetidin-1-yl]-3-methyl-butyl-3-enoic acid benzhydryl ester 
• 122661-93-2 2α-methyl-2β-[(1,2,3-triazol-1-yl)methyl]penicillin-3α-carboxylic acid diphenylmethyl ester 
• 89786-04-9 tazobactam 
• 87579-79-1 (R)-benzhydryl 2-((R)-2-(benzo[d]thiazol-2-yldisulfanyl)-4-oxoazetidin-1-yl)-3-methylbut-3-enoate 
• 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 
• 182750-65-8 benzhydryl 2β-hydroxymethyl-1,1-dioxopenicillanate 
• 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 
• 182750-64-7 benzhydryl 2β-(chloroacetoxy)methyl-1,1-dioxo-penicillanate 
• 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 
• 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 
• 89786-04-9 tazobactam acid 
• 85573-73-5 2β-(chloro)methyl-2α-methyl-6,6-dihydropenam-3α-carboxylic 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 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

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

Method for preparing penam sulfoxide acid diphenyl methyl ester which is tazobactam precursor

The invention provides a method for preparing penam sulfoxide acid diphenyl methyl ester. The method includes steps of carrying out bromination reaction on 6-aminopenicillanic acid to obtain first reaction products; carrying out reaction on the first reac

Crystal structures of KPC-2 β-lactamase in complex with 3-nitrophenyl boronic acid and the penam sulfone PSR-3-226

Class A carbapenemases are a major threat to the potency of carbapenem antibiotics. A widespread carbapenemase, KPC-2, is not easily inhibited by β-lactamase inhibitors (i.e., clavulanic acid, sulbactam, and tazobactam). To explore different mechanisms of inhibition of KPC-2, we determined the crystal structures of KPC-2 with two β-lactamase inhibitors that follow different inactivation pathways and kinetics. The first complex is that of a small boronic acid compound, 3-nitrophenyl boronic acid (3-NPBA), bound to KPC-2 with 1.62-A resolution. 3-NPBA demonstrated a Km value of 1.0±0.1 μM (mean±standard error) for KPC-2 and blocks the active site by making a reversible covalent interaction with the catalytic S70 residue. The two boron hydroxyl atoms of 3-NPBA are positioned in the oxyanion hole and the deacylation water pocket, respectively. In addition, the aromatic ring of 3-NPBA provides an edge-to-face interaction with W105 in the active site. The structure of KPC-2 with the penam sulfone PSR-3-226 was determined at 1.26-A resolution. PSR-3-226 displayed a Km value of 3.8±0.4 μM for KPC-2, and the inactivation rate constant (k inact) was 0.034±0.003 s-1. When covalently bound to S70, PSR-3-226 forms a trans-enamine intermediate in the KPC-2 active site. The predominant active site interactions are generated via the carbonyl oxygen, which resides in the oxyanion hole, and the carboxyl moiety of PSR-3-226, which interacts with N132, N170, and E166. 3-NPBA and PSR-3-226 are the first β-lactamase inhibitors to be trapped as an acyl-enzyme complex with KPC-2. The structural and inhibitory insights gained here could aid in the design of potent KPC-2 inhibitors. Copyright

PROCESS FOR PRODUCING PENICILLANIC ACID COMPOUND

A process for preparing a penicillanic acid compound of the formula (2) comprising reacting a halogenated penicillanic acid compound of the formula (1), (a) in the presence of a metal bismuth or bismuth compound, (b) with a metal having a lower standard o

A new approach to the synthesis of tazobactam using an organosilver compound

Tazobactam (9) was synthesized in 8 steps from the readily accessible 6-APA. By the first use of silver triazole as reactant, the formation of the isomer 7 was avoided and a total yield of 50%, which was two to three times higher than that of reported procedures for 9, was obtained. Georg Thieme Verlag Stuttgart.

STEREOSELECTIVE SYNTHESIS OF 6α-HALOPENICILLANATES BY SAMARIUM(II) IODIDE PROMOTED REDUCTION OF 6,6-DIHALOPENICILLANATES

A mild an efficient samarium(II) iodide promoted-reduction of 6,6-dibromopenicillanates for stereoselective synthesis of 6α-bromopenicillanates has been developed.