76646-91-8

Basic information

• Product Name: (3S)-6,6-DIBROMO-2,2-DIMETHYLPENAM-3-CARBOXYLIC ACID 1,1-DIOXIDE
• Synonyms: 6,6-DibroMopenicillanic Acid S,S-Dioxide;SulbactaM Related CoMpound E;(3S)-6,6-DIBROMO-2,2-DIMETHYLPENAM-3-CARBOXYLIC ACID 1,1-DIOXIDE;6,6-Dibromo-3,3-dimethyl-7-oxo-4,4-dioxide (2S-bis)-4-thia-1-azabicyclo-(3,2,0)-heptane-2-carbonoic acid;Sulbactam EP Impurity E
• CAS NO: 76646-91-8
• Molecular Formula: C₈H₉Br₂NO₅S
• Molecular Weight: 391.03
• EINECS: 427-200-4
• Product Categories: Heterocycles;Impurities;Intermediates & Fine Chemicals;Pharmaceuticals;Sulfur & Selenium Compounds;Heterocycles, Impurities, Pharmaceuticals, Intermediates & Fine Chemicals, Sulfur & Selenium Compounds
• Mol File: 76646-91-8.mol
• Article Data: 18

Chemical Properties

• Melting Point: 177-178 °C (decomp)
• Boiling Point: 600.1°C at 760 mmHg
• Flash Point: 316.8°C
• Appearance: /
• Density: 2.29g/cm³
• Vapor Pressure: 5.95E-16mmHg at 25°C
• Refractive Index: 1.685
• PKA: 2.03±0.60(Predicted)
• CAS DataBase Reference: (3S)-6,6-DIBROMO-2,2-DIMETHYLPENAM-3-CARBOXYLIC ACID 1,1-DIOXIDE(CAS DataBase Reference)
• NIST Chemistry Reference: (3S)-6,6-DIBROMO-2,2-DIMETHYLPENAM-3-CARBOXYLIC ACID 1,1-DIOXIDE(76646-91-8)
• EPA Substance Registry System: (3S)-6,6-DIBROMO-2,2-DIMETHYLPENAM-3-CARBOXYLIC ACID 1,1-DIOXIDE(76646-91-8)

Safety Data

• Hazardous Substances Data: 76646-91-8(Hazardous Substances Data)

Usage

Description

(3S)-6,6-DIBROMO-2,2-DIMETHYLPENAM-3-CARBOXYLIC ACID 1,1-DIOXIDE, also known as 6,6-Dibromopenicillanic Acid S,S-Dioxide, is a chemical compound derived from the semi-synthetic β-lactamase inhibitor Sulbactam (S699185). It is characterized by its unique molecular structure, which includes a 3-carboxylic acid group, a 1,1-dioxide group, and two bromine atoms at the 6,6-positions. (3S)-6,6-DIBROMO-2,2-DIMETHYLPENAM-3-CARBOXYLIC ACID 1,1-DIOXIDE is typically found as an impurity in the production process of Sulbactam.

Uses

Used in Pharmaceutical Industry:
(3S)-6,6-DIBROMO-2,2-DIMETHYLPENAM-3-CARBOXYLIC ACID 1,1-DIOXIDE is used as an impurity in the production of the semi-synthetic β-lactamase inhibitor Sulbactam (S699185) for its role in enhancing the effectiveness of certain antibiotics. As an impurity, it is essential to monitor and control its presence to ensure the safety and efficacy of the final pharmaceutical product.
In the context of Sulbactam, this compound serves as a reminder of the importance of quality control and purity in the pharmaceutical manufacturing process. While it may not have a direct application as a therapeutic agent, its presence in the production of Sulbactam highlights the need for thorough analysis and purification of active pharmaceutical ingredients to maintain the highest standards of patient care.

InChI:InChI=1/C8H9Br2NO5S/c1-7(2)3(4(12)13)11-5(14)8(9,10)6(11)17(7,15)16/h3,6H,1-2H3,(H,12,13)/t3-,6+/m0/s1

Upstream product

• 36091-15-3 (5R,6R)-6-amino-2,2-dimethyl-1,1-dioxopenam-3-carboxylic acid 
• 24158-88-1 6,6-dibromopenicillanic acid 
• 551-16-6 6-Aminopenicillanic Acid 
• 76454-48-3 Sodium 6,6-dibromopenicillanate 
• 205320-24-7 6,6-dibromopenicillanic acid 

Downstream Products

• 68373-14-8 sulbactum 
• 75527-87-6 6β-bromopenicillanic acid 1,1-dioxide 
• 75527-88-7 (2S,5R,6S)-6β-bromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid,S,S-dioxide 
• 68373-14-8 sulbactam 
• 122661-92-1 p-methoxybenzyl 6,6-dibromopenicillinate 1,1-dioxide 
• 81324-43-8 (2S,5R)-6,6-dibromo-3,3-dimethyl-4,4,7-trioxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid diphenylmethyl ester 
• 854139-74-5 (3,3-dimethyl-4,4,7-trioxo-4-thia-1-azabicyclo[3.2.0]hept-2-yl)phenylselenylacetaldehyde 
• 854139-75-6 2-[[1,3]dioxolan-2-yl(phenylselenyl)methyl]-3,3-dimethyl-4,4-dioxo-4-thia-1-azabicyclo[3.2.0]heptan-7-one 
• 305796-42-3 (2S,5R,6R)-3,3-dimethyl-4,4,7-trioxo-6-(2-oxo-ethyl)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid diphenylmethyl ester 
• 176220-76-1 (2S,5R,6R)-3,3-dimethyl-4,4,7-trioxo-6-(2-propenyl)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid diphenylmethyl ester 
• 305796-43-4 (2S,5R,6R)-3,3-dimethyl-4,4,7-trioxo-6-(2-hydroxylimino-ethyl)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid diphenylmethyl ester 
• 305796-41-2 (2S,5R,6R)-6-bromo-3,3-dimethyl-4,4,7-trioxo-6-(2-propenyl)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid diphenylmethyl ester 
• 305796-45-6 (2S,5R,6R)-3,3-Dimethyl-4,4,7-trioxo-6-oxycyanomethyl-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester 
• 305796-44-5 (2S,5R,6R)-3,3-dimethyl-4,4,7-trioxo-6-(2-chloro-2-hydroxylimino-ethyl)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid diphenylmethyl ester 

Relevant articles and documents

A versatile strategy for the solid-phase synthesis of penicillin derivatives: Efficient preparation of 2β-methyl substituted penams as β-lactamase inhibitor analogues

A convenient solid-phase method for the synthesis of 2β-methyl substituted penicillins using commercially available resins is described. Functionalization of Merrifield and Wang resin bound penam derivatives was performed by penicillin sulfoxide rearrangement and the products were released from the supports under mild conditions. The utility of this methodology has been demonstrated by synthesizing a small library of penicillin derivatives in moderate to very good overall isolated yields for the multistep synthetic sequence. Georg Thieme Verlag Stuttgart.

Synthesis method of sulbactam

The invention relates to a synthesis method of sulbactam, and belongs to the field of beta-lactamase inhibitor synthesis. In the method, 6-aminopenicillanic acid (6-APA) as a raw material is dissolvedin an organic solvent, and is adopted together with bromine as substrates under a strong acid condition, 6,6-dibromo penicillanic acid is formed through diazotization bromination in a manner of dropwise adding a sodium nitrite solution, and then one-step oxidation and reduction are performed to obtain sulbactam. According to the method, a hydrogen peroxide one-step oxidation mode is adopted, andthe use of potassium permanganate is avoided from the source, so that the generation of waste salt is reduced, and meanwhile, the use of a large amount of ethyl acetate is avoided. The method not onlyreduces the emission of three wastes from the source and greatly reduces the emission of organic matters and waste salt in the original process, but also greatly reduces the side reaction and the rawmaterial cost.

Method for preparing sulbactam acid

The invention relates to the field of pharmaceutical synthesis and provides a method for preparing sulbactam acid. The method is used for solving the problem of the traditional synthesis methods thatthe yield is low. The method comprises the following steps: S1. diazotation and bromination reaction: adding bromine, a dilute sulfuric acid solution and sodium nitrite solids into 6-aminopenicillanicacid, so as to obtain a first intermediate, wherein the dilute sulfuric acid solution adopts depleted deuterium water as a solvent; S2. oxidation reaction: dropwise adding potassium permanganate anda dilute sulfuric acid solution into the first intermediate, so as to obtain a second intermediate; and S3. hydrogenation reaction: add strontium powder and a dilute sulfuric acid solution into the second intermediate, thereby obtaining a product, i.e., the sulbactam acid, wherein the dilute sulfuric acid solution adopts depleted deuterium water as a solvent. Through preparing the dilute sulfuricacid solution by adopting the depleted deuterium water as the solvent and adopting the strontium powder as a catalyst, the improvement on reaction activity of dilute sulfuric acid is facilitated, theconversion ratio of reaction is increased, and thus, the increase of reaction yield is facilitated, so that the yield of reaction can be higher than 90%.

Sulbactam sodium compound containing one-twentieth water and pharmaceutical composition thereof

The invention discloses a sulbactam sodium compound containing one-twentieth water. The sulbactam sodium compound is white crystalline powder, and each mole of sulbactam sodium contains one-twentiethmole of water. The sulbactam sodium compound has main diffraction peaks at the positions with the corresponding main X-ray characteristic diffraction peak 2 theta angle of 14.23+/-0.2 degrees, 17.76+/-0.2 degrees, 19.22+/-0.2 degrees, 23.09+/-0.2 degrees, 24.60+/-0.2 degrees and 27.86+/-0.2 degrees. The sulbactam sodium compound prepared by means of a method has high stability and meets the requirements for being used a raw material of a preparation.