(2s,5r,6s)-6-Bromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

Base Information

• Chemical Name: (2s,5r,6s)-6-Bromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
• CAS No.: 24138-28-1
• Molecular Formula: C8H10 Br N O3 S
• Molecular Weight: 280.142
• European Community (EC) Number: 246-028-9
• DSSTox Substance ID: DTXSID101122521
• Nikkaji Number: J242.738I
• Mol file: 24138-28-1.mol

Synonyms:24138-28-1;(2s,5r,6s)-6-bromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid;EINECS 246-028-9;C8H10BrNO3S;C8-H10-Br-N-O3-S;(2S-(2alpha,5alpha,6alpha))-6-Bromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid;SCHEMBL9557741;DTXSID101122521;[2S-(2alpha,5alpha,6alpha)]-6-bromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid;AKOS030242158;(2S,5beta)-6beta-Bromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2beta-carboxylic acid

Chemical Property of (2s,5r,6s)-6-Bromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

Chemical Property:

• Boiling Point: 462.6°Cat760mmHg
• PKA: 2.43±0.50(Predicted)
• Flash Point: 233.6°C
• PSA: 82.91000
• Density: 1.84g/cm³
• LogP: 0.83470
• Solubility.: Methanol
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 278.95648
• Heavy Atom Count: 14
• Complexity: 320

Purity/Quality:

99% ^*data from raw suppliers

6α-BromopenicillanicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(C(N2C(S1)C(C2=O)Br)C(=O)O)C
• Isomeric SMILES: CC1([C@@H](N2[C@H](S1)[C@H](C2=O)Br)C(=O)O)C
• 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.

Technology Process of (2s,5r,6s)-6-Bromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

There total 9 articles about (2s,5r,6s)-6-Bromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 91.0%

6-Aminopenicillanic Acid (551-16-6) → 6-bromopenicillanic acid (24138-28-1)

Guidance literature:

6-Aminopenicillanic Acid; With sulfuric acid; potassium bromide; In ethanol; at 0 - 5 ℃;

With sodium nitrite; In ethanol; at 0 - 5 ℃;

DOI:10.1055/s-2004-837299

Reference yield: 90.0%

6-aminopenicillanic acid (21794-93-4) → 6-bromopenicillanic acid (24138-28-1)

Guidance literature:

With sulfuric acid; potassium bromide; In ethanol; at 4 - 8 ℃;

Reference yield: 72.0%

6-aminopenicillanic acid (551-16-6,1079-37-4,3115-55-7,21794-93-4,145920-51-0) → 6-bromopenicillanic acid (24138-28-1)

Guidance literature:

With sulfuric acid; sodium bromide; sodium nitrite; In methanol; water; at 0 - 2 ℃; for 0.5h;

DOI:10.1039/P19800002322

upstream raw materials:

6-Aminopenicillanic Acid

6-aminopenicillanic acid

6,6-dibromopenicillanic acid

6-aminopenicillanic acid

Downstream raw materials:

Benzyl 6α-bromopenicillanate

tazobactam acid

(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

6α-bromopenicillan-3α-carboxylic acid diphenylmethyl ester-1β-oxide

Refernces

• 1、 Cignarella,Pifferi,Testa. "-". . p. 2668. Retrieved 1962.
• 2、 Ke, Wei,Bethel, Christopher R.,Papp-Wallace, Krisztina M.,Pagadala, Sundar Ram Reddy,Nottingham, Micheal,Fernandez, Daniel,Buynak, John D.,Bonomo, Robert A.,Van Den Akker, Focco. "Crystal structures of KPC-2 β-lactamase in complex with 3-nitrophenyl boronic acid and the penam sulfone PSR-3-226". scheme or table. p. 2713 - 2718. Retrieved 2012/08/27.
• 3、 Xu, Wei Liang,Li, Yun Zheng,Zhang, Qing Shan,Zhu, He Sun. "A new approach to the synthesis of tazobactam using an organosilver compound". . p. 442 - 446. Retrieved 2007/10/03.