87579-79-1

Basic information

• Product Name: (R)-benzhydryl 2-((R)-2-(benzo[d]thiazol-2-yldisulfanyl)-4-oxoazetidin-1-yl)-3-methylbut-3-enoate
• Synonyms: (R)-benzhydryl 2-((R)-2-(benzo[d]thiazol-2-yldisulfanyl)-4-oxoazetidin-1-yl)-3-methylbut-3-enoate
• CAS NO: 87579-79-1
• Molecular Weight: 532.708
• Mol File: 87579-79-1.mol

Chemical Properties

• CAS DataBase Reference: (R)-benzhydryl 2-((R)-2-(benzo[d]thiazol-2-yldisulfanyl)-4-oxoazetidin-1-yl)-3-methylbut-3-enoate(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-benzhydryl 2-((R)-2-(benzo[d]thiazol-2-yldisulfanyl)-4-oxoazetidin-1-yl)-3-methylbut-3-enoate(87579-79-1)
• EPA Substance Registry System: (R)-benzhydryl 2-((R)-2-(benzo[d]thiazol-2-yldisulfanyl)-4-oxoazetidin-1-yl)-3-methylbut-3-enoate(87579-79-1)

Safety Data

• Hazardous Substances Data: 87579-79-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
(R)-Benzhydryl 2-((R)-2-(benzo[d]thiazol-2-yldisulfanyl)-4-oxoazetidin-1-yl)-3-methylbut-3-enoate is used as an intermediate in the synthesis of 4-Sulfonylazetidin-2-ones, which are compounds known for their anti-cancer properties. The chiral nature of this compound allows for the development of targeted therapies that can selectively affect cancer cells while minimizing damage to healthy cells.
Used in Antibiotic Enhancement:
(R)-benzhydryl 2-((R)-2-(benzo[d]thiazol-2-yldisulfanyl)-4-oxoazetidin-1-yl)-3-methylbut-3-enoate is also utilized in the synthesis of Tazobactam Sodium Salt-15N3 (T010103), a labeled analogue of Tazobactam Sodium Salt (T010100). Tazobactam is a β-Lactamase inhibitor, which is used in combination with β-lactam antibiotics to enhance their effectiveness against bacteria that produce β-lactamase enzymes. The inclusion of this compound in the synthesis process helps to improve the overall efficacy of the resulting antibiotic formulations.

Upstream product

• 149-30-4 2-Mercaptobenzothiazole 
• 80353-26-0 6α-bromopenicillan-3α-carboxylic acid diphenylmethyl ester-1β-oxide 
• 87579-78-0 diphenylmethyl (2S,5R,6R)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate 4-oxide 
• 24138-28-1 6-bromopenicillanic acid 
• 100349-41-5 (2S,4S,5R,6S)-6-bromo-3,3-dimethyl-4,7-dioxo-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylic acid benzhydryl ester 
• 5350-57-2 benzophenone hydrazone 
• 551-16-6 6-Aminopenicillanic Acid 
• 100349-42-6 (2S,4S,5R)-3,3-dimethyl-4,7-dioxo-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylic acid benzhydryl ester 
• 205320-26-9 6α-Bromopenicillanic acid 
• 80353-26-0 Benzhydryl 6α-bromopenicillanate-1-oxide 
• 551-16-6 6-aminopenicillanic acid 
• 74189-25-6 diphenylmethyl 6α-bromopenicillanate 
• 205320-23-6 benzhydryl-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate-4-oxide 

Downstream Products

• 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 
• 162515-56-2 Benzhydryl (E)-(2S,3S,5R)-3-methyl-4,4,7-trioxo-3-(2-thiazol-2-yl-vinyl)-4-thia-1-aza-bicyclo [3.2.0]heptane-2-carboxylate 
• 162515-57-3 benzhydryl (Z)-(2S,3S,5R)-3-methyl-4,4,7-trioxo-3-(2-thiazol-2-yl-vinyl)-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylate 
• 162514-85-4 benzhydryl (E)-(2S,3S,5R)-3-(2-carbamoyl-vinyl)-3-methyl-4,4,7-trioxo-4-thia-1-aza-bicyclo [3.2.0]heptane-2-carboxylate 
• 162515-54-0 (2S,3S,5R)-3-Methyl-7-oxo-3-((E)-2-thiazol-2-yl-vinyl)-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester 
• 162515-55-1 (2S,3S,5R)-3-Methyl-7-oxo-3-((Z)-2-thiazol-2-yl-vinyl)-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester 
• 162515-03-9 (2S,3S,5R)-3-((E)-2-Chloro-vinyl)-3-methyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester 
• 162515-04-0 benzhydryl (Z)-(2S,3S,5R)-3-(2-chloro-vinyl)-3-methyl-4,4,7-trioxo-4-thia-1-aza-bicyclo [3.2.0]heptane-2-carboxylate 

Relevant articles and documents

PENAM DERIVATIVES FOR TREATING BACTERIAL INFECTIONS

Novel iron chelating group conjugated penam derivatives described herein show antibacterial activity, and could be used as antibacterial agents or beta-lactamase inhibitors (BLIs) which are of value for application in combination with other antibacterial

2 β -triazole methylpenicillanic acid dibenzoate. Preparation method of tazobactam intermediate and tazobactam

The invention provides a preparation method of 2 β -triazole methyl penicillanic acid dibenzoate, tazobactam intermediate and tazobactam. The preparation method comprises the following steps: reacting a reaction raw material comprising a double-sulfur ring opening compound, 1, 2, 3 - triazole and first oxidizing agent in first solvent to obtain a product system comprising 2 β - triazole methylpenicillanic acid dibenzoate. The structural formula of 2 β -triazole methylpenicillanic acid dibenzoate is shown. Under the action first oxidizing agent 1, 2 and 3 - triazole are used for directly closing the bicyclic ring opening compound, and the efficient and high-selectivity synthesis of the bis-sulfur ring-opening compound directly to the key intermediate 2 β - triazole methylpenicillanic acid dibenzoate is successfully realized. Further, 2 β - triazole methyl penicillanic acid dibenzoate is used as a key intermediate for synthesizing tazobactam, the yield of tazobactam is improved, and the cost is reduced.

2 β - Azidomethyl penicillanic acid dibenzoate. Preparation method of tazobactam intermediate and tazobactam

The invention provides a preparation method of 2 β -azipenicillanic acid dibenzoate, tazobactam intermediate and tazobactam. The preparation method comprises the following steps: carrying out free radical reaction in a solvent by using a reaction raw material comprising a double-sulfur open-loop compound, a stacked nitrogen source and an oxidant to obtain a product system comprising 2 β - azidomethyl penicillanic acid dibenzoate. By radical addition of the carbon-carbon double bonds of the double-sulfur ring-opening compound through the azide free radical, high-efficiency and high-selectivity synthesis of the disulphide ring-opening compound directly to 2 β - azimaapenem naphthenate is successfully realized through intramolecular radical substitution. Further, 2 β - azidomethyl penicillanic acid dibenzoate is taken as a key intermediate for synthesizing tazobactam, the yield of tazobactam is improved, and the cost is reduced.

Continuous synthesis method of tazobactam intermediate

The invention provides a continuous synthesis method of a tazobactam intermediate. The device adopted by the continuous synthesis method comprises a continuous reaction device and a heat exchange device, wherein the heat exchange device is used for adjust

Preparation method of tazobactam

The invention discloses a preparation method of tazobactam. The preparation method comprises the following steps: performing double oxidization on 2beta-chloromethyl penicillanic acid diphenyl methylester by adopting a solution prepared from potassium permanganate, glacial acetic acid and concentrated sulfuric acid; then loading triazole by taking crown ether as a phase transfer catalyst and taking potassium iodide as a catalyst; then performing deprotection to obtain tazobactam. Compared with the prior art, the preparation method disclosed by the invention has the advantages that although sulfur atoms are oxidized into sulfone to lower chlorine atom activity, the use of the crown ether as the phase transfer catalyst and the potassium iodide as the catalyst compensates for the inactivation well. By adopting the method, the stability of the 2beta-chloromethyl penicillanic acid diphenyl methyl ester is improved, the reaction time is shortened, the reaction yield is improved, the operation risk is lowered, and the industrial production is facilitated.

Synthetic method of tazobactam acid

The invention provides a synthetic method of tazobactam acid, comprising the steps of (a) using 6-APA (6-aminopenicillanic acid) as a starting material and cetyltrimethylammonium hydrogensulfate as a catalyst to oxidize with oxone to obtain compound A; subjecting the compound A to deamination reaction to obtain compound B; esterifying the compound B to obtain compound C; (b) subjecting the compound C and 2-mercaptobenzothiazole to reduced pressure backflow to obtain compound D; ultrasonically vibrating the compound D and copper bromide to obtain compound E; reacting the compound E and 1H-1,2,3-triazole to obtain compound F; (c) allowing hydrogen peroxide and acetic anhydride to act on the compound F to obtain compound G; reacting the compound G with anisole to obtain tazobactam acid. Amino groups in 6-APA are diazotized directly, diazo groups are then removed, reduced pressure backflow and ultrasonic vibration are performed, hydrogen peroxide and acetic anhydride are used as oxidants, less byproducts are generated, and the yield and quality of tazobactam acid are effectively increased.

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

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.

Design, synthesis, and evaluation of 2β-alkenyl penam sulfone acids as inhibitors of β-lactamases

A general method for synthesis of 2β-alkenyl penam sulfones has been developed. The new compounds inhibited most of the common types of β- lactamase. The level of activity depended very strongly on the nature of the substituent in the 2β-alkenyl group. Th