491878-07-0

Basic information

• Product Name: (4R,5S,6S)-3-[[(3S,5S)-5-[[(Aminosulfonyl)amino]methyl]-1-[[(4-nitrophenyl)methoxy]carbonyl]-3-pyrrolidinyl]thio]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid (4-nitrophenyl)methyl ester
• Synonyms: (4R,5S,6S)-3-[[(3S,5S)-5-[[(Aminosulfonyl)amino]methyl]-1-[[(4-nitrophenyl)methoxy]carbonyl]-3-pyrrolidinyl]thio]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid (4-nitrophenyl)methyl ester;Doripenem Condensation Compound;Doripenem condensate;4-nitrobenzyl (4R,5S,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-3-[[(3S,5S)-1-(4-nitrobenzyloxycarbonyl)-5-(sulfamoylaminomethyl)pyrrolidin-3-yl]thio]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate;(4R,5S,6S)-3-[[(3S,5S)-5-[[(Aminosulfonyl)amino]methyl]-1-[[(4-nitrophenyl)methoxy]carbonyl]-3-pyrrolidinyl]thio]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-o
• CAS NO: 491878-07-0
• Molecular Formula: C₃₀H₃₄N₆O₁₂S₂
• Molecular Weight: 734.75
• EINECS: 1533716-785-6
• Mol File: 491878-07-0.mol

Chemical Properties

• Melting Point: 160-180 °C (decomp)
• Boiling Point: 950.289 °C at 760 mmHg
• Flash Point: 528.516 °C
• Appearance: /
• Density: 1.597 g/cm³
• PKA: 10.91±0.60(Predicted)
• CAS DataBase Reference: (4R,5S,6S)-3-[[(3S,5S)-5-[[(Aminosulfonyl)amino]methyl]-1-[[(4-nitrophenyl)methoxy]carbonyl]-3-pyrrolidinyl]thio]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid (4-nitrophenyl)methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (4R,5S,6S)-3-[[(3S,5S)-5-[[(Aminosulfonyl)amino]methyl]-1-[[(4-nitrophenyl)methoxy]carbonyl]-3-pyrrolidinyl]thio]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid (4-nitrophenyl)methyl ester(491878-07-0)
• EPA Substance Registry System: (4R,5S,6S)-3-[[(3S,5S)-5-[[(Aminosulfonyl)amino]methyl]-1-[[(4-nitrophenyl)methoxy]carbonyl]-3-pyrrolidinyl]thio]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid (4-nitrophenyl)methyl ester(491878-07-0)

Safety Data

• Hazardous Substances Data: 491878-07-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(4R,5S,6S)-3-[[(3S,5S)-5-[[(Aminosulfonyl)amino]methyl]-1-[[(4-nitrophenyl)methoxy]carbonyl]-3-pyrrolidinyl]thio]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid (4-nitrophenyl)methyl ester is used as a potential antibacterial agent for its ability to target and inhibit bacterial growth, making it a candidate for the development of new antibiotics to combat resistant strains of bacteria.
Used in Medicinal Chemistry Research:
In the field of medicinal chemistry, this compound is utilized for its unique structural features and potential to be modified or optimized for various therapeutic applications. Its specific configuration and functional groups offer opportunities for the design of novel drugs with improved efficacy and selectivity.

Upstream product

• 93711-81-0 (4-nitrophenyl)methyl (4R,5R,6S)-3-[(diphenoxyphosphinyl)oxy]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate 
• 148017-03-2 (2S,4S)-4-mercapto-2-(N-sulfamoyl-aminomethyl)-1-(4-nitrobenzyloxycarbonyl)pyrrolidine 
• 491878-06-9 (2S,4S)-4-acetylthio-2-[[N-aminosulfonyl-N-(tert-butyloxycarbonyl)amino]methyl]pyrrolidine-1-carboxylic acid p-nitrobenzyl 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 
• 90822-24-5 (γR,2R,3S)-α-diazo-3-[(1R)-1-hydroxyethyl]-γ-methyl-β,4-dioxo-2-azetidinebutanoic acid (4-nitrophenyl)methyl ester 

Downstream Products

• 364622-82-2 (+)-(4R,5S,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-3-[[(3S,5S)-5-(sulfamoylaminomethyl)pyrrolidin-3-yl]thio]-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid monohydrate 
• 148016-81-3 doripenem 

Relevant articles and documents

A method for preparing Doripenem (by machine translation)

The invention relates to a method for preparing donipenem as well as, by acetyl thio pyrrolidine derivatives (SM-1) as the starting material, by removing acetyl and uncle butoxycarbonyl make mercat pyrrolidine derivatives (DN-1), then and [...]south parent nucleus (SM-2, MAP) is prepared by nucleophilic substitution reaction Doripenem of protection, then catalytic hydrogenation removes PNZ, protection PNB, refined Doripenem final product. The solvent used in the method and the catalyst can be recycled, thereby greatly saving the production cost, suitable for the large-scale industrial production. (by machine translation)

DORIPENEM INTERMEDIATE COMPOUND, PREPARATION PROCESS THEREFOR AND USE THEREOF, AND PREPARATION PROCESS FOR DORIPENEM

The present invention provides a doripenem intermediate compound shown by formula (XIV), wherein PNB is p-nitrobenzyl, and HX is an acid; and when HX is a monobasic acid, n=1; and when HX is a polybasic acid, n=2. The present invention also provides a process for preparing the doripenem intermediate compound (XIV). In addition, the present invention provides a process for preparing doripenem (I) from the doripenem intermediate compound (XIV) in a simple manner, with a high yield and low production costs. The new mono-protected doripenem intermediate compound provided in the present invention contains only one protecting group, reducing the difficulty and complexity in the subsequent de-protection step by catalytic hydrogenation, increasing the yield of the catalytic hydrogenation reaction, and thus reducing the production cost of the final product. The process is easy to operate and suitable for industrialized production.

Crystalline form doripenem monohydrate and preparation method thereof

The present invention relates to a method for preparing doripenem monohydrate, and more particularly, to a method for preparing doripenem monohydrate produced through the steps of: conducting a deprotecting reaction by reacting doripenem-PNB with a zinc powder in a mixture solution including an organic solvent and an aqueous phosphate solution (step 1); removing phosphate from the product of step 1 (step 2); and crystallizing the product of step 2 using a solvent for crystallization to crystallize the doripenem monohydrate (step 3). According to the method for preparing the doripenem monohydrate, the method can be conducted at room temperature and at a moderate atmospheric pressure without using an expensive metal catalyst and special equipment. Thus, the method is economical and safe, and the doripenem monohydrate can be obtained at a high yield. Accordingly, the preparation method of the present invention can be usefully applied in an industrial field related to doripenem monohydrate.

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.

Preparation of Carbapenem Intermediate and Their Use

The present invention relates to preparing carbapenem intermediates that are useful to produce Ertapenem, Meropenem and Doripenem.

A PROCESS FOR THE PREPARATION OF DORIPENEM

The present invention provides processes for the preparation of doripenem and for the preparation of doripenem in amorphous form.

Practical Large-Scale Synthesis of Doripenem: A Novel 1β- Methylcarbapenem Antibiotic

A practical large-scale process for the synthesis of doripenem hydrate (1), a novel parenteral 1β-methylcarbapenem antibiotic, from p-nitrobenzyl-protected enolphosphate 2b and N-(p-nitrobenzyloxycarbonyl)- protected aminomethylpyrrolidine 3c is described. We found effective extraction conditions to remove p-toluidine and most other organic impurities using a THF/ water system containing an inorganic salt. Significant improvements have been made to the previous synthesis using a medicinal chemical procedure. The new process requires no chromatographic purification and affords the target compound 1 as a sterile crystalline powder. Several kilograms of compound 1 were successfully prepared by this process.

Pyrrolidylthiocarbapenem derivative

A pyrrolidylthiocarbapenem derivative represented by Formula I is provided: STR1 wherein R1 is hydrogen or lower alkyl; R2, R3 and R4 are hydrogen, lower alkyl which can be substituted or an amino protecting group independently, or R2 and R3 together with a nitrogen atom to which R2 and R3 are bonded form a saturated or unsaturated cyclic group, or R2 and R4, or R3 and R4 together with two nitrogen atoms and one sulfur atom in the sufamide group form a saturated or unsaturated cyclic group; each cyclic group can further include at least one atom selected from the group consisting of oxygen, sulfur and nitrogen, and each cyclic group can be substituted; X1 is hydrogen or a hydroxy protecting group; X2 is hydrogen, a carboxy protecting group, an ammonio group, an alkali metal or an alkaline-earth metal; and Y2 is hydrogen or an amino protecting group.