57943-82-5

Basic information

• Product Name: Methyl
• Synonyms: Methyl;-)-(o-chlorophenyl)-4,5-dihydrothieno[2,3-c]pyridine-6(7H)-acetate, hydrochloride;(2R,3Z,5R)-3-(2-Hydroxyethylidene)-7-oxo-4-oxa-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid Methyl Ester;[2R-(2α,3Z,5α)]- 3-(2-Hydroxyethylidene)-7-oxo-4-oxa- 1-azabicyclo[3.2.0]heptane-2-carboxylic Acid Methyl Ester;Clavulanic Acid Methyl Ester;3,4-Methylenedioxy AMphetaMine-d6 Hydrochloride
• CAS NO: 57943-82-5
• Molecular Formula: C₉H₁₁NO₅
• Molecular Weight: 15.03452
• Product Categories: Amines;Heterocycles;Inhibitors;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 57943-82-5.mol

Chemical Properties

• Boiling Point: 425.6±45.0 °C(Predicted)
• Appearance: /
• Density: 1.46±0.1 g/cm3(Predicted)
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility: DMSO (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
• PKA: 13.43±0.10(Predicted)
• Stability: Temperature Sensitive
• CAS DataBase Reference: Methyl(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl(57943-82-5)
• EPA Substance Registry System: Methyl(57943-82-5)

Safety Data

• Hazardous Substances Data: 57943-82-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Methyl is used as a β-lactamase inhibitor for Clavulanic Acid Methyl Ester, which is a substituted Clavulanic acid. This application helps in enhancing the effectiveness of antibiotics by preventing the degradation of β-lactam antibiotics by bacterial enzymes.
Used in Controlled Substances:
Methyl is used as a labelled metabolite of MDMA (3,4-methylenedioxy-N-methylamphetamine), which is an entactogen and a synthetic amphetamine derivative with stimulant and hallucinogenic properties. It is classified as a controlled substance due to its hallucinogenic effects.
Used in Chemical Reactions:
Methyl is used as a functional group in various chemical reactions, contributing to the formation of a wide range of organic compounds. Its presence in molecules can significantly influence their properties and reactivity, making it an essential component in the synthesis of numerous pharmaceuticals, agrochemicals, and other industrial products.

Upstream product

• 186581-53-3 diazomethane 
• 58001-44-8 clavulanic acid 
• 67-56-1 methanol 
• 57943-84-7 Benzyl Clavulanate 
• 74-88-4 methyl iodide 
• 57943-81-4 potassium clavulanate 
• 72510-78-2 (5RS)-7-oxo-3-(3Ξ)-[1,2,4]trioxolan-3-yl(Z)methylene-(5rH)-4-oxa-1-aza-bicyclo[3.2.0]heptane-2c-carboxylic acid methyl ester 
• 68290-19-7 (2-methylsulfanyl-4-oxo-azetidin-1-yl)-acetic acid methyl ester 
• 64455-19-2 3-(Z)-allylidene-7-oxo-(5rH)-4-oxa-1-aza-bicyclo[3.2.0]heptane-2c-carboxylic acid methyl ester 

Downstream Products

• 63612-78-2 methyl (2R,5R)-3-oxoethylidene-7-oxo-4-oxa-1-azabicyclo<3.2.0>heptane-2-carboxylate 
• 63699-74-1 methyl (2R,5R)-3-oxoethylidene-7-oxo-4-oxa-1-azabicyclo<3.2.0>heptane-2-carboxylate 
• 57943-81-4 potassium clavulanate 
• 59897-38-0 methyl dihydroclavulanate 
• 102101-33-7 methyl (1S,5R,7R)-3-oxo-6-trifluoroacetyl-1-vinyl-2,8-dioxa-6-azabicyclo<3.2.1>octane-7-carboxylate 
• 63617-41-4 9-O-(N-methylcarbamoyl)clavulanic acid 
• 60802-60-0 phenacyl isoclavulanate 
• 63617-43-6 benzyl 9-O-carbamoylclavulanate 
• 63617-40-3 benzyl 9-O-(N-methylcarbamoyl)clavulanate 
• 63617-42-5 benzyl 9-O-(N-phenylcarbamoyl)clavulanate 
• 60802-61-1 benzyl isoclavulanate 
• 63699-73-0 benzyl (2R,5R)-3-oxoethylidene-7-oxo-4-oxa-1-azabicyclo<3.2.0>heptane-2-carboxylate 
• 63612-77-1 benzyl (2R,5R)-3-oxoethylidene-7-oxo-4-oxa-1-azabicyclo<3.2.0>heptane-2-carboxylate 
• 60297-60-1 p-bromobenzyl clavulanate 

Relevant articles and documents

Clavulanic Acid and its Derivatives. Structure Elucidation of Clavulanic Acid and the Preparation of Dihydroclavulanic Acid, Isoclavulanic acid, Esters and Related Oxidation Products

Clavulanic acid, a novel β-lactamase inhibitor from Streptomyces clavuligerus, has been shown to be Z-(2R,5R)-3-(β-hydroxyethylidene)-7-oxo-4-oxa-1-azabicycloheptane-2-carboxylic acid (1).The structure and absolute stereochemistry was confirmed by X-ray analysis of the p-nitrobenzyl and p-bromobenzyl esters, (14) and (15).The conversion of clavulanic acid into a variety of esters and acyl derivatives is described.An account of its isomerisation to the E isomer (30) and the formation of an oxetane (45) as a by-product of the photolysis of the phenacyl ester (18) is given.The reduction and oxidation of acid (1) under a variety of conditions has also been examined in detail.

Oxidative Decarboxylation of Clavulanic Acid and Its 9-Methyl Ether

The carboxy group of clavulanic acid has been replaced by a methoxy group, an acetoxy group, and a m-chlorobenzoyloxy group using standard methods for oxidative decarboxylation (electrolysis, reaction with lead tetra-acetate, and decarboxylative rearrangement of a diacyl peroxide, respectively).In an unexpected reaction, 9-O-methylclavulanic acid (20) reacted with p-chlorophenylselenenyl bromide and base to give 3-(p-chlorophenylseleno)-2-(2-methoxyethylidene)clavam (21).Refluxing a solution of compound (21) in toluene gave 3-hydroxy-2-(2-methoxyethylidene)clavam and b is(p-chlorophenyl)diselenide, the overall result being the replacement of the carboxy group in the acid (20) by a hydroxy group.In chloroform, this 3-hydroxyclavam exists predominantly as the ring-opened aldehyde.Possible mechanisms for the formation of the seleno derivative (21) and its decomposition in refluxing toluene are discussed.

A new total synthesis of (±)-clavulanic acid

Regioselective reactions at the terminal double bond of the racemic azetidinone dienylether (4), provides a source of clavulanic acid and several analogues.