76247-40-0

Basic information

• Product Name: chloromethyl (2S-cis)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate 4,4-dioxide
• Synonyms: chloromethyl (2S-cis)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate 4,4-dioxide;(2S,5R)-3,3-Dimethyl-4,4,7-trioxo-4-thia(VI)-1-azabicyclo[3.2.0]heptane-2-carboxylic acid chloromethyl ester
• CAS NO: 76247-40-0
• Molecular Formula: C₉H₁₂ClNO₅S
• Molecular Weight: 281.71328
• EINECS: 278-401-7
• Mol File: 76247-40-0.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 491.258°C at 760 mmHg
• Flash Point: 250.904°C
• Appearance: /
• Density: 1.565g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.571
• CAS DataBase Reference: chloromethyl (2S-cis)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate 4,4-dioxide(CAS DataBase Reference)
• NIST Chemistry Reference: chloromethyl (2S-cis)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate 4,4-dioxide(76247-40-0)
• EPA Substance Registry System: chloromethyl (2S-cis)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate 4,4-dioxide(76247-40-0)

Safety Data

• Hazardous Substances Data: 76247-40-0(Hazardous Substances Data)

Usage

General Description

Chloromethyl (2S-cis)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate 4,4-dioxide, also known as cefaclor, is a second-generation cephalosporin antibiotic used to treat bacterial infections. It functions by inhibiting the formation of the bacteria's cell wall, leading to their destruction. Cefaclor is effective against a wide range of bacteria, making it a commonly prescribed medication for conditions such as urinary tract infections, respiratory tract infections, and skin infections. However, it is important to use cefaclor only as prescribed by a healthcare professional, as misuse or overuse of antibiotics can lead to the development of antibiotic resistance. Cefaclor may also cause side effects such as diarrhea, nausea, and allergic reactions in some individuals.

InChI:InChI=1/C9H12ClNO5S/c1-9(2)7(8(13)16-4-10)11-5(12)3-6(11)17(9,14)15/h6-7H,3-4H2,1-2H3/t6-,7+/m1/s1

Upstream product

• 49715-04-0 chlorosulfuric acid chloromethyl ester 
• 76350-35-1 potassium penicillanate 1,1-dioxide 
• 593-71-5 Chloroiodomethane 
• 68373-14-8 sulbactum 
• 69388-84-7 sodium sulbactam 
• 74-97-5 chlorobromomethane 
• 76350-37-3 chloromethyl 6α-chloropenicillanate 1,1-dioxide 
• 144-55-8 sodium hydrogencarbonate 
• 688-73-3 tri-n-butyl-tin hydride 
• 7439-96-5 manganese 
• 84458-09-3 chloromethyl 6,6-dibromopenicillanate 1,1-dioxide 
• 7440-48-4 cobalt 

Downstream Products

• 84519-07-3 6'-(2-Benzyloxycarbonylamino-2-phenylacetamido)-penicillanoyloxymethyl Penicillanate 1,1-Dioxide 
• 103063-56-5 6'-(2-[4-nitrobenzyloxycarbonylamino]-2-[4-hydroxyphenyl]acetamido)penicillanoyloxymethyl penicillanate 1,1-dioxide 
• 103063-55-4 6'-(2-[4-Nitrobenzyloxycarbonylamino]-2phenylacetamido)penicillanoyloxymethyl penicillanate 1,1-dioxide 
• 76247-39-7 iodomethyl penicillanate 1,1-dioxide 
• 84519-06-2 6'-(2,2-dimethyl-4-phenyl-5-imidazolidinon-1-yl)-penicillanoyloxymethyl penicillanate 1,1-dioxide 

Relevant articles and documents

Synthesis method and application of amoxicillin and sulbactam hybrid molecule

The invention discloses a synthesis method and application of an amoxicillin and sulbactam hybrid molecule, and belongs to the technical field of organic synthesis. According to the method, chlorobromomethane is used as a chloromethyl reagent of sulbactam acid, so that the yield of a key intermediate sulbactam chloromethyl ester is effectively increased, and sulbactam chloromethyl ester and (Z)-6-(2-(4-hydroxyphenyl)-2-((4-methoxy-4-oxobutyl-2-ene-2-yl) amino) acetamido)-3, 3'-dihydroxyl-7-oxo-4-sulfo-1-azabicyclo[3.2.0]heptane-2-carboxylic acid as a raw material to carry out condensation reaction, and a protecting group is removed by using strong acid, so as to prepare the amoxicillin and sulbactam hybrid molecule. The synthesis method has the advantages of mild reaction conditions, cheap and easily available raw materials, low preparation cost, good safety, simple and feasible process and high product yield.

Procedure for the preparation of dioxopenicillanic acid derivatives

Procedure for the preparation of dioxopenicillanic acid derivatives and its salts pharmaceutically acceptable with general formula I, where, R is hydrogen, alkyl group containing 1 to 5 Carbon atoms or a residue of type -CH2R ', where R ' is hydrogen, halogen or a p-toluensulfonyl group. These are prepared by treatment of the compounds of general formula II, where R is as previously defined and X may be hydrogen or bromine, with a metallic reagent constituted by a mixture or alloy of copper and/or cobalt and/or manganese with iron and/or nickel in an aqueous/organic medium. These compounds are useful as inhibitors of beta-lactamase.

Process and intermediates for preparation of 1,1-dioxopenicillanoyloxymethyl 6-beta-aminopenicillanate

A process for the preparation of 1,1-dioxopenicillanoyloxymethyl 6-beta-aminopenicillanate which comprises reacting 1,1-dioxopenicillanoyloxymethyl 6-phenylacetamidopenicillanate or the corresponding phenoxyacetamidopenicillanate under anhydrous conditions with a halogenating agent in the presence of a reaction inert solvent to form an intermediate imino halide, addition of a primary alcohol having from one to four carbon atoms to convert the imino halide to an imino ether and subsequent hydrolysis to give the desired product.