85573-73-5

Basic information

• Product Name: (2S,5R)-3α-Chloromethyl-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2β-carboxylic acid benzhydryl ester
• Synonyms: (2S,5R)-3α-Chloromethyl-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2β-carboxylic acid benzhydryl ester
• CAS NO: 85573-73-5
• Molecular Formula: C₂₁H₂₀ClNO₃S
• Molecular Weight: 401.9064
• Mol File: 85573-73-5.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 565.1±50.0 °C(Predicted)
• Appearance: /
• Density: 1.36±0.1 g/cm3(Predicted)
• PKA: -3.84±0.60(Predicted)
• CAS DataBase Reference: (2S,5R)-3α-Chloromethyl-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2β-carboxylic acid benzhydryl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,5R)-3α-Chloromethyl-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2β-carboxylic acid benzhydryl ester(85573-73-5)
• EPA Substance Registry System: (2S,5R)-3α-Chloromethyl-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2β-carboxylic acid benzhydryl ester(85573-73-5)

Safety Data

• Hazardous Substances Data: 85573-73-5(Hazardous Substances Data)

Usage

Description

(2S,5R)-3α-Chloromethyl-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2β-carboxylic acid benzhydryl ester is a complex organic compound with a unique molecular structure. It is characterized by its chiral centers at the 2S and 5R positions, a chloromethyl group at the 3α position, and a methyl group at the 3 position. The molecule also contains a 7-oxo group and a 4-thia-1-azabicyclo[3.2.0]heptane ring system. The benzhydryl ester group is attached to the carboxylic acid moiety, which is located at the 2β position. (2S,5R)-3α-Chloromethyl-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2β-carboxylic acid benzhydryl ester serves as an important intermediate in the synthesis of pharmaceuticals, particularly β-lactamase inhibitors.

Uses

Used in Pharmaceutical Industry:
(2S,5R)-3α-Chloromethyl-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2β-carboxylic acid benzhydryl ester is used as an intermediate in the synthesis of Tazobactam Sodium Salt-15N3 (T010103), a β-lactamase inhibitor. This inhibitor is used in combination with β-lactam antibiotics to enhance their effectiveness against bacterial infections. By inhibiting the β-lactamase enzymes produced by bacteria, Tazobactam Sodium Salt-15N3 helps to prevent the degradation of β-lactam antibiotics, allowing them to exert their antibacterial action more effectively.

Upstream product

• 85573-72-4 (R)-2-[2-(benzothiazol-2-yldisulfanyl)-4-oxo-azetidin-1-yl]-3-methyl-butyl-3-enoic acid benzhydryl ester 
• 87579-78-0 diphenylmethyl (2S,5R,6R)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate 4-oxide 
• 73968-83-9 benzhydryl 6,6-dihydropenicillate 
• 87579-79-1 (R)-benzhydryl 2-((R)-2-(benzo[d]thiazol-2-yldisulfanyl)-4-oxoazetidin-1-yl)-3-methylbut-3-enoate 
• 85573-72-4 2-oxo-4-(benzothiazol-2-yl)dithio-α-isopropenyl-1-azetidine acetic acid benzhydryl ester 
• 205320-26-9 6α-Bromopenicillanic acid 
• 80353-26-0 Benzhydryl 6α-bromopenicillanate-1-oxide 
• 205320-23-6 benzhydryl-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate-4-oxide 
• 551-16-6 6-aminopenicillanic acid 

Downstream Products

• 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 
• 122661-93-2 2α-methyl-2β-[(1,2,3-triazol-1-yl)methyl]penicillin-3α-carboxylic acid diphenylmethyl ester 
• 1379595-05-7 C₂₆H₂₈N₃O₅S⁽¹⁺⁾*I^(1-) 
• 1379595-04-6 (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 

Relevant articles and documents

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.

Preparation technologies of tazobactam acid and tazobactam diphenylmethyl ester and application

The invention relates to preparation technologies of tazobactam acid and tazobactam diphenylmethyl ester and application. A preparation route is as follows: with methylbenzene, 2-mercaptobenzothiazoleand a debrominated product as starting materials, the tazobactam diphenylmethyl ester is prepared after a ring opening reaction, a chlorination reaction, a condensation reaction and a double oxidation reaction, then the tazobactam diphenylmethyl ester is transformed into the tazobactam acid after a deprotection reaction; a preparation method in the scheme is improved on the basis of an iodinationreaction in the prior art, and the chlorination reaction is introduced, so that the reaction quality is optimized, the product purity is improved, and use of toxic, harmful, flammable and explosive substances in the reaction process is reduced, and thus the reaction is more environment-friendly; the product yield can be as high as 98-99.92%, and the preparation cost is also lower than that of thepreparation technology in the prior art.

Synthesis of penicillin derivatives and study of their cytotoxic properties

By the interaction of heterocyclic thiols with sulforides of 6,6-dihydro- and 6α-chloropenicillanates, derivatives of 4-heteryldithio-2-azetidinones have been synthesized, as well as products of their cyclization to form 2β-heterylthiomethyl-and 2β-halorn