76497-76-2

Basic information

• Product Name: 3-chloro-1-carbacephem
• Synonyms: 3-chloro-1-carbacephem
• CAS NO: 76497-76-2
• Molecular Formula: C₈H₉ClN₂O₃
• Molecular Weight: 0
• Mol File: 76497-76-2.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 431.3°C at 760 mmHg
• Flash Point: 214.6°C
• Appearance: /
• Density: 1.64g/cm³
• Vapor Pressure: 1.2E-08mmHg at 25°C
• Refractive Index: 1.658
• CAS DataBase Reference: 3-chloro-1-carbacephem(CAS DataBase Reference)
• NIST Chemistry Reference: 3-chloro-1-carbacephem(76497-76-2)
• EPA Substance Registry System: 3-chloro-1-carbacephem(76497-76-2)

Safety Data

• Hazardous Substances Data: 76497-76-2(Hazardous Substances Data)

Usage

InChI:InChI=1/C8H9ClN2O3/c9-3-1-2-4-5(10)7(12)11(4)6(3)8(13)14/h4-5H,1-2,10H2,(H,13,14)/t4-,5+/m1/s1

Upstream product

• 124594-03-2 tert-butyl (6R*,7S*)-3-chloro-7-phthalylimido-8-oxo-1-azabicyclo<4.2.0>oct-2-en-2-carboxylate 
• 86686-58-0 (6R,7S)-7-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-8-oxo-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl ester 
• 607691-22-5 3-[(2R,3S)-3-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-1-(4-nitro-benzyloxycarbonylmethyl)-4-oxo-azetidin-2-yl]-propionic acid phenyl ester 
• 607691-20-3 3-[(2R,3S)-3-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-1-(4-nitro-benzyloxycarbonylmethyl)-4-oxo-azetidin-2-yl]-propionic acid 
• 607691-24-7 (6R,7S)-7-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-3-hydroxy-8-oxo-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-nitro-benzyl ester 
• 139165-12-1 (6R,7S)-3-Chloro-7-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-8-oxo-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-nitro-benzyl ester 
• 124594-04-3 (6R*,7S*)-3-chloro-7-phthalylimido-8-oxo-1-azabicyclo<4.2.0>oct-2-en-2-carboxylic acid 
• 76470-65-0 (6R*,7S*)-3-chloro-7-phenylacetamido-8-oxo-1-azabicyclo<4.2.0>oct-2-en-2-carboxylic acid 
• 75390-24-8 tert-butyl (6R*,7S*)-3-chloro-7-amino-8-oxo-1-azabicyclo<4.2.0>oct-2-en-2-carboxylate 
• 139165-13-2 (6R,7S)-3-Chloro-7-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-8-oxo-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 
• 1217259-23-8 (6R,7S)-3-chloro-8-oxo-7-((R)-2-phenyl-2-(3-phenylthioureido)acetamido)-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 
• 140866-88-2 3-{(2R,3S)-1-(4-Nitro-benzyloxycarbonylmethyl)-4-oxo-3-[2-(pyrrolidine-1-carbonyl)-benzoylamino]-azetidin-2-yl}-propionic acid phenyl ester 
• 140866-89-3 (6R,7S)-3-Hydroxy-8-oxo-7-[2-(pyrrolidine-1-carbonyl)-benzoylamino]-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-nitro-benzyl ester 
• 140866-87-1 3-{(2R,3S)-4-Oxo-1-phenoxycarbonylmethyl-3-[2-(pyrrolidine-1-carbonyl)-benzoylamino]-azetidin-2-yl}-propionic acid phenyl ester 

Downstream Products

• 76470-65-0 (6R*,7S*)-3-chloro-7-phenylacetamido-8-oxo-1-azabicyclo<4.2.0>oct-2-en-2-carboxylic acid 
• 76609-94-4 (6R,7S)-7-[(R)-2-Amino-2-(4-hydroxy-phenyl)-acetylamino]-3-chloro-8-oxo-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 
• 76470-66-1 loracarbef 

Relevant articles and documents

CARBACEPHEM BETA-LACTAM ANTIBIOTICS

Carbacephem β-lactam antibiotics having structure (I) are disclosed, including stereoisomers, pharmaceutically acceptable salts, esters and prodrugs thereof, wherein Ar2, X, R1 and R2 are as defined herein. The compounds are useful for the treatment of bacterial infections, in particular those caused by methicillin-resistant Staphylococcus spp.

Methods and compounds for the preparation of carbacephems

A chiral process for preparing compounds of the formula: STR1 from a compound of the formula: STR2 in which the compound formula (IV) is reacted with trimethylsilyl iodide to remove the chiral auxiliary at the 7-position and the carboxy protecting group. The process allows for the retention of the amino and carboxy protecting groups throughout the preparation of Compound IV. Also disclosed are novel intermediates.

Synthesis and biological evaluation of 3-chloro-1-carbacephem compounds

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