24138-28-1

Basic information

• Product Name: [2S-(2alpha,5alpha,6alpha)]-6-bromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
• Synonyms: [2S-(2alpha,5alpha,6alpha)]-6-bromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid;(2S,5β)-6β-Bromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2β-carboxylic acid;(2S-(2alpha,5alpha,6alpha))-6-Bromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid;Einecs 246-028-9;SulbactaM Related CoMpound (6-alfa-BroMopenicillanic acid)
• CAS NO: 24138-28-1
• Molecular Formula: C₈H₁₀BrNO₃S
• Molecular Weight: 280.1389
• EINECS: 246-028-9
• Mol File: 24138-28-1.mol
• Article Data: 14

Chemical Properties

• Boiling Point: 462.6°Cat760mmHg
• Flash Point: 233.6°C
• Appearance: /
• Density: 1.84g/cm³
• Solubility: Methanol
• PKA: 2.43±0.50(Predicted)
• CAS DataBase Reference: [2S-(2alpha,5alpha,6alpha)]-6-bromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: [2S-(2alpha,5alpha,6alpha)]-6-bromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid(24138-28-1)
• EPA Substance Registry System: [2S-(2alpha,5alpha,6alpha)]-6-bromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid(24138-28-1)

Safety Data

• Hazardous Substances Data: 24138-28-1(Hazardous Substances Data)

Usage

Uses

6α-Bromopenicillanic acid 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

• 24158-88-1 6,6-Dibromopenicillanic acid 
• 24158-88-1 6,6-dibromopenicillanic acid 
• 21794-93-4 6-aminopenicillanic acid 
• 551-16-6 6-aminopenicillanic acid 
• 551-16-6 6-Aminopenicillanic Acid 

Downstream Products

• 69388-78-9 (2S,5R)-Benzyl 3,3-Dimethyl-7-oxo-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate 4,4-Dioxide 
• 100239-31-4 p-nitrobenzyl 6-bromopenicillanate 
• 62263-89-2 Benzyl 6α-bromopenicillanate 
• 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 
• 80353-26-0 6α-bromopenicillan-3α-carboxylic acid diphenylmethyl ester-1β-oxide 
• 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 
• 75527-87-6 6β-bromopenicillanic acid 1,1-dioxide 
• 72554-59-7 1β-oxo-1λ⁴-penicillanic acid 4-nitro-benzyl ester 
• 73634-04-5 1β-oxo-1α-phthalimidoimino-1λ⁶-penicillanic acid 4-nitro-benzyl ester 
• 76454-56-3 benzyl bromopenicillanate-S,S-dioxide 
• 80078-08-6 6α-bromopenam-3α-carboxylic acid benzyl ester-1β-oxide 
• 76911-22-3 6,6-dihydropenam-3α-carboxylic acid benzyl ester-1β-oxide 

Relevant articles and documents

On the chemistry of beta-lactamase inhibition by 6 beta-bromopenicillanic acid.

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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.

Process for preparation of penam derivatives

The invention relates to novel processes for preparing penam derivatives, such as Tazobactam and derivatives thereof. The processes according to the invention encompass procedures for the protection and deprotection of the carboxylic group as well as for the oxidation of the sulphur moiety of penam derivatives. Additionally, the present invention relates to new intermediates for the production of penam derivatives, allowing the desired penam-derivatives to be formulated with high purity and in good yields.

PROCESS FOR PREPARING 6-ALKYLIDENE PENEM DERIVATIVES

The present invention provides a process of making compounds of Formula (I), which are useful for the treatment of bacterial infection or disease.