115922-43-5

Basic information

• Product Name: 4-BROMO-2-(METHOXYIMINO)-3-OXOBUTYRYLCHLORIDE
• Synonyms: 4-BROMO-2-(METHOXYIMINO)-3-OXOBUTYRYLCHLORIDE
• CAS NO: 115922-43-5
• Molecular Formula: C5H5 Br Cl N O3
• Molecular Weight: 242.46
• Mol File: 115922-43-5.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 4-BROMO-2-(METHOXYIMINO)-3-OXOBUTYRYLCHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-BROMO-2-(METHOXYIMINO)-3-OXOBUTYRYLCHLORIDE(115922-43-5)
• EPA Substance Registry System: 4-BROMO-2-(METHOXYIMINO)-3-OXOBUTYRYLCHLORIDE(115922-43-5)

Safety Data

• Hazardous Substances Data: 115922-43-5(Hazardous Substances Data)

Upstream product

• 79232-66-9 (Z)-4-bromo-2-methoxyimino-3-oxo-butyric acid 
• 79-37-8 oxalyl dichloride 
• 68-12-2 N,N-dimethyl-formamide 
• 10026-13-8 phosphorus pentachloride 

Relevant articles and documents

A NOVEL INTERMEDIATE FOR THE PREPARATION OF CEFEPIME

A novel process is disclosed for preparation of cefepime, a cephalosporin antibiotic in two steps comprising of (i) acylation of 7-Amino-3-[(1-methyl-1-pyrrolidinium)methyl]-3-cephem-4-carboxylate hydrochloride (IV) with 4-bromo-2-methoxyimino-3-oxobutyric acid chloride (III) to give 7-(4-bromo-2-methoxyimino-3-oxobutyramido)-3--[(1-methyl-1-pyrrolidinium)methyl]-3-cephem-4-carboxylate (II), (ii) cyclisation of bromo compound II with thiourea to give cefepime (I) and (iii) purification of cefepime.

Process for preparing cefepime

A novel process is disclosed for the preparation of Cefepime, a cephalosporin antibiotic, using novel new intermediates of the general Formula, where X represents Bromine or Chlorine atom This process comprises the step of cyclizing the bromo or chloro intermediate with thiourea to produce Cefepime of high purity. A process to prepare bromo or chloro intermediate comprising the acylation of 7-Amino-3-[(1-methyl-1-pyrrolidinium) methyl]-3-cephem-4-carboxylate with 4-halo-2-methoxyimino-3-oxobutyric acid halide is also described.

Method for manufacture of ceftriaxone sodium

An improved process for preparation of ceftriaxone sodium of formula (II), is disclosed.

Ceftiofur, its intermediate and a process for the preparation of the same

A novel process for the preparation of ceftiofur, a cephalosporin antibiotic useful in the treatment of bovine respiratory disease. The process utilizes a new bromo or chloro intermediate that can be isolated in a pure form by this inventive process subsequently resulting in ceftiofur of high purity. This invention offers a new-to-the-world route to Ceftiofur using novel intermediates.

4-halogeno-2-oxyimino-3-oxobutyric acids and derivatives

A method of producing a 4-halo-2-(substituted or unsubstituted)hydroxyimino-3-oxobutyric acid ester or amide, which is a synthetic intermediate of value for the production of cephalosporins containing an aminothiazole group, characterized by reacting a 2-(substituted or unsubstituted)-hydroxyimino-3-oxobutyric acid or an ester or amide thereof with a silylating agent and reacting the resulting novel 2-(substituted)hydroxyimino-3-silyloxy-3-butenoic acid ester or amide with a halogenating agent.

Acyl derivatives

There are presented compounds of the formula STR1 wherein R1 is one of the 3-substituents usable in cephalosporin chemistry, R2 is hydrogen, lower alkyl or COOR3 -lower alkyl, wherein R3 is hydrogen, a cation of a base or a readily hydrolyzable ester group, and X is sulphur, oxygen or one of the groups --SO-- and --SO2 --, and the readily hydrolyzable esters, readily hydrolyzable ethers and salts of these compounds and hydrates of the compounds of formula I or of their esters, ethers and salts, also presented are methods for the manufacture of these compounds as well as compounds used in their manufacture.

3-Thiovinyl-cephalosporins

Novel cephalosporins of the general formula (I); STR1 in which R is alkyl, L-2-amino-2-carboxy-ethyl, phenyl, pyridyl, pyridyl-N-oxide, pyrimidin-2-yl, substituted pyridazin-3-yl, 5,6-dioxo-1,4,5,6-tetrahydro-1,2,4-triazin-3-yl substituted in the 4-position, 1,3,4-triazol-5-yl or 2-alkoxycarbonyl-1,3,4-triazol-5-yl substituted in the 1-position, 1,4-dialkyl-5,6-dioxo-1,4,5,6-tetrahydro-1,2,4-triazin-3-yl, 1-alkyl-5,6-dioxo-1,4,5,6-tetrahydro-1,2,4-triazin-3-yl, 2-alkyl-5,6-dioxo-1,2,5,6-tetrahydro-1,2,4-triazin-3-yl, triazol-5-yl, 1,3,4-thiadiazol-5-yl which is substituted or unsubstituted, 1,2,4-thiadiazol-5-yl which is substituted, 1,3,4-oxadiazol-5-yl which is substituted or unsubstituted, oxazol-2-yl which is substituted or unsubstituted or tetrazol-5-yl which is substituted or unsubstituted in the 1-position, R' is a hydrogen atom or a radical of the general formula (II); STR2 and Ro is hydrogen, alkyl, vinyl or cyanomethyl, as well as their salts, are useful as anti-bacterial agents.

3-Vinyl-cephalosporins

Novel 3-vinyl-cephalosporins of the formula STR1 in which n is 0 or 1, R1 is hydrogen, a radical of the formula STR2 [in which R4 is hydrogen or a protective radical and R5 is hydrogen, alkyl, vinyl or cyanomethyl or is a protective radical], or a protective radical, and R2 is hydrogen, a protective radical or an enzymatically removable radical, or R1 is hydrogen or an acyl radical which may carry various substituents and R2 is hydrogen or a protective radical, and R3 is a radical of the general formula R'3 --SO2 --O-- or R"3 --CO--O--, in which R'3 is alkyl, trifluoromethyl, trichloromethyl or phenyl which is substituted by a halogen atom or by an alkyl or nitro radical, and R"3 is defined like R'3 or represents methyl which is substituted by acyl or alkoxycarbonyl, or represents ethyl or propyl substituted in the 2-position by acyl or alkoxycarbonyl. These compounds are useful as intermediates for the preparation of antibiotic 3-thiovinyl-cephalosporins.