189188-38-3

Basic information

• Product Name: 4-Nitrobenzyl (4S,5R,6S)-3-[(diphenylphosphono)oxy]-6-[(R)-1-hydroxyethyl]- 4-Methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate
• Synonyms: 4-Nitrobenzyl (4S,5R,6S)-3-[(diphenylphosphono)oxy]-6-[(R)-1-hydroxyethyl]- 4-Methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate;STULDTCHQXVRIX-NUQURWJTSA-N
• CAS NO: 189188-38-3
• Molecular Formula: C29H27N2O10P
• Molecular Weight: 594.505841
• Product Categories: Aromatics, Pharmaceuticals, Intermediates & Fine Chemicals, Chiral Reagents
• Mol File: 189188-38-3.mol
• Article Data: 14

Chemical Properties

• Boiling Point: 722.4±60.0 °C(Predicted)
• Appearance: /
• Density: 1.47±0.1 g/cm3(Predicted)
• PKA: 14.36±0.20(Predicted)
• CAS DataBase Reference: 4-Nitrobenzyl (4S,5R,6S)-3-[(diphenylphosphono)oxy]-6-[(R)-1-hydroxyethyl]- 4-Methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Nitrobenzyl (4S,5R,6S)-3-[(diphenylphosphono)oxy]-6-[(R)-1-hydroxyethyl]- 4-Methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate(189188-38-3)
• EPA Substance Registry System: 4-Nitrobenzyl (4S,5R,6S)-3-[(diphenylphosphono)oxy]-6-[(R)-1-hydroxyethyl]- 4-Methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate(189188-38-3)

Safety Data

• Hazardous Substances Data: 189188-38-3(Hazardous Substances Data)

Usage

Description

4-Nitrobenzyl (4S,5R,6S)-3-[(diphenylphosphono)oxy]-6-[(R)-1-hydroxyethyl]-4-Methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate is a complex organic compound with a unique molecular structure. It is characterized by its nitrobenzyl group, diphenylphosphonooxy group, and hydroxyethyl group, which contribute to its chemical properties and potential applications.

Uses

Used in Pharmaceutical Industry:
4-Nitrobenzyl (4S,5R,6S)-3-[(diphenylphosphono)oxy]-6-[(R)-1-hydroxyethyl]-4-Methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate is used as an intermediate for the production of Carbapenem antibiotics. These antibiotics are known for their broad-spectrum activity against various types of bacteria, making them valuable in the treatment of a wide range of infections.
Used in Antibiotic Production:
4-Nitrobenzyl (4S,5R,6S)-3-[(diphenylphosphono)oxy]-6-[(R)-1-hydroxyethyl]-4-Methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate is specifically used as an intermediate in the synthesis of Meropenem, an injectable antibiotic. Meropenem is effective in treating severe bacterial infections, particularly those caused by antibiotic-resistant strains, due to its strong bactericidal activity and ability to penetrate bacterial cell walls.

Upstream product

• 90822-23-4 (3S,4R)-3-<(1R)-1-hydroxyethyl>-4-<(1R)-1-methyl-3-p-nitrobenzyloxycarbonyl-2-oxopropyl>-2-azetidin-2-one 
• 93711-85-4 (2R)-2-[(2S,3S)-3-{(1R)-1-(t-butyldimethylsilyloxy)ethyl}-4-oxoazetidin-2-yl]propionic acid 
• 90822-22-3 (3S,4R)-3-<(1R)-1-<(tert-Butyldimethylsilyl)oxy>ethyl>-4-<(1R)-1-methyl-3-(p-nitrobenzyloxycarbonyl)-2-oxopropyl>azetidin-2-one 
• 105995-50-4 magnesium 4-nitrobenzyl malonate 
• 77359-11-6 propanedioic acid mono[(4-nitrophenyl)methyl] ester 
• 90822-25-6 p-nitrobenzyl (1R,5S,6S)-6-<(R)-1-hydroxyethyl>-1-methyl-2-oxo-carbapanem-3-carboxylate 
• 2524-64-3 chlorophosphoric acid diphenyl ester 
• 104873-15-6 4-nitrobenzyl (4R,5R,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-3,7-dioxo-1-azabicyclo[3.2.0]-heptane-2-carboxylate 
• 101765-69-9 (S)-2-{(2S,3S)-3-[1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-thiopropionic acid S-phenyl ester 
• 86978-81-6 Acetic acid (2R,3R)-3-[1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-1-trimethylsilanyl-azetidin-2-yl ester 
• 90776-58-2 (S)-2-{(2S,3S)-3-[1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-propionic acid 
• 83973-55-1 (2R,4S,5R,6S)-6-(1-Hydroxy-ethyl)-4-methyl-3,7-dioxo-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 4-nitro-benzyl ester 
• 101765-69-9 (R)-2-{(2S,3S)-3-[1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-thiopropionic acid S-phenyl ester 
• 90776-58-2 (R)-2-{(2S,3S)-3-[1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-propionic acid 

Downstream Products

• 192884-06-3 (4R,5S,6S)-6-((R)-1-Hydroxy-ethyl)-4-methyl-7-oxo-3-(pyrrolidine-1-carbonylsulfanyl)-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester 
• 161715-24-8 tebipenem pivoxil 
• 161715-24-8 tebipenem 
• 148016-81-3 doripenem 

Relevant articles and documents

Improved process for the preparation of carbapenem using carbapenem intermediates and recovery of carbapenem

The present invention relates to preparing carbapenem intermediates that are useful to produce Ertapenem, Meropenem and Doripenem; and provides an effective process for recovering ertapenem compounds.

PROCESS FOR THE PREPARATION OF CARBAPENEM COMPOUNDS

The present invention relates to a process for the preparation of carbapenem compound of Formula (I), wherein P1 is hydrogen or a carboxyl protecting group, P3 is hydrogen or a hydroxyl protecting group, R1 is C1-3 alkyl, and A is selected from a group consisting of a) Formula (II), b) Formula (III), c) Formula (IV), d) Formula (V), e) Formula (VI), f) Formula (VII), wherein P2 is hydrogen or an amino protecting group, R2 and R3 may be same or different and are hydrogen, C1-5 alkyl, optionally substituted aryl, or optionally substituted heteroaryl, and X1 is O or S, or its stereoisomers, or salts thereof.

IMPROVED METHOD FOR THE CRYSTALLIZATION OF INTERMEDIATES OF CARBAPENEM ANTIBIOTICS

The present invention relates to an azetidinone compound extremely useful as a common intermediate for the synthesis of 1β-methylcarbapenem compounds. The present invention provides a crystallization method to obtain a crystal which has a higher quality and a higher stability than a conventional crystal and is excellent in filterability at the time of recovering crystal; an azetidinone compound having a low content of impurity; and an azetidinone compound which has a controlled particle size distribution of crystals and improved handleability and stability. The crystallization is carried out by adding a hydrocarbon solvent to a solution in which an azetidinone compound extremely useful as a common intermediate for the synthesis of 1β-methylcarbapenem compounds is dissolved in the presence of a seed crystal in an amount of 200% by weight or less based on the weight of the azetidinone compound. According to the method, the crystal having a high quality and a high stability and excellent filterability at the time of recovering the crystal can be obtained.