148017-03-2

Usage

Uses

Used in Pharmaceutical Industry:
(2R,4S)-4-nitrobenzyl 4-Mercapto-2-((sulfaMoylaMino)Methyl)pyrrolidine-1-carboxylate is used as a potential antimicrobial agent for the development of new drugs to combat bacterial infections. The presence of the sulfaMoylaMino group, a derivative of the antibiotic sulfonamide, suggests its potential effectiveness in treating bacterial infections.
Used in Organic Synthesis:
(2R,4S)-4-nitrobenzyl 4-Mercapto-2-((sulfaMoylaMino)Methyl)pyrrolidine-1-carboxylate is used as a reagent in organic synthesis due to the presence of the mercapto group, which is commonly used in chemical assays and has a strong odor.
Used in Chemical Assays:
(2R,4S)-4-nitrobenzyl 4-Mercapto-2-((sulfaMoylaMino)Methyl)pyrrolidine-1-carboxylate is used as a reagent in chemical assays, taking advantage of the mercapto group's properties for various analytical purposes.

InChI:InChI=1/C13H18N4O6S2/c14-25(21,22)15-6-11-5-12(24)7-16(11)13(18)23-8-9-1-3-10(4-2-9)17(19)20/h1-4,11-12,15,24H,5-8H2,(H2,14,21,22)/t11-,12-/m0/s1

Upstream product

• 148017-06-5 (2S,4S)-1-p-nitrobenzyloxycarbonyl-2-aminomethyl-4-mercaptopyrrolidine 
• 101803-29-6 (2S,4R)-4-hydroxy-2-methoxycarbonyl-1-(4-nitrobenzyloxycarbonyl)pyrrolidine 
• 138324-82-0 (2S,4R)-4-mesyloxy-1-(p-nitrobenzyloxycarbonyl)pyrrolidine-2-carboxylic acid methyl ester 
• 96034-97-8 (2S,4S)-4-acetylthio-2-methoxycarbonyl-1-p-nitrobenzyloxycarbonylpyrrolidine 
• 148017-02-1 (2S,4S)-1-p-nitrobenzyloxycarbonyl-2-sulfamoylaminomethyl-4-tritylthiopyrrolidine 
• 491878-06-9 (2S,4S)-4-acetylthio-2-[[N-aminosulfonyl-N-(tert-butyloxycarbonyl)amino]methyl]pyrrolidine-1-carboxylic acid p-nitrobenzyl ester 

Downstream Products

• 491878-07-0 (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 
• 148016-81-3 doripenem 

Relevant academic research and scientific papers

Preparation method for synthesizing doripenem side chain intermediate

The invention discloses a preparation method for synthesizing a doripenem side chain intermediate. The preparation method comprises the following steps: dissolving a compound IV serving as an initialraw material in an organic solvent I, and introducing am

A method for preparing Doripenem

The invention belongs to the field of medicine synthesis and particularly relates to a doripenem preparation method. The method includes the steps that a compound 5 reacts with concentrated sulfuric acid in methanol to obtain a compound 4; the compound 4 and p-Nitrobenzyl-6-(1-hydroxyethyl)-1-azabicyclo(3.2.0)heptane-3,7-dione-2-carboxylate (a compound 3) are subjected to a condensation reaction under the condition that N,N-diisopropylethylamine exists, water and ethyl acetate are added and stirred after the reaction, an ethyl acetate layer is collected, alcohol is added in ethyl acetate collection liquid, crystallization is carried out, and a compound 2 is obtained; the product is dissolved through ethyl acetate; after a monopotassium phosphate solution and a phase transfer reagent of triethylbenzylammonium chloride are added, zinc powder is added into the ethyl acetate/monopotassium phosphate solution in batches to react and obtain doripenem. According to the method, reaction conditions are moderate, the technology is simple, and the conversion rate and the yield are high. Two-phase reaction is used in deprotection reaction, and the after-treatment process is simplified. The zinc powder which is cheap is used, so that the method is economical, and a new concept and a new method are provided for doripenem preparation.

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)

AN IMPROVED PROCESS FOR THE PREPARATION OF PYRROLIDINE THIOL DERIVATIVES USEFUL IN THE SYNTHESIS OF CARBAPENEM COMPOUNDS

The present invention relates to an improved process for the preparation of the compound of formula (III) which is used in the synthesis of carbapenem antibiotics. wherein R3 is hydrogen or an amine protecting group.

AN IMPROVED PROCESS FOR THE PREPARATION OF CARBAPENEM ANTIBIOTIC

The present invention relates to an improved process for the preparation of the carbapenem antibiotic of formula (I) or its salts, hydrates and esters. The present invention further provides novel crystalline form of compound of general formula (III), wherein R3 is p-nitrobenzyloxy carbonyl.

A PROCESS FOR THE PREPARATION OF CARBAPENEM COMPOUNDS

The present invention relates to an improved process for the preparation of carbapenem compounds.

Deacetylation of thioacetate using acetyl chloride in methanol

A highly efficient method for the deacetylation of thioacetate is reported under mild acidic conditions employing acetyl chloride in methanol. Some of the major advantages are mild conditions, high efficiency, high yields, and easy operations. Copyright Taylor & Francis Group, LLC.

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.