138324-82-0

Basic information

• Product Name: 1,2-Pyrrolidinedicarboxylic acid, 4-[(Methylsulfonyl)oxy]-, 2-Methyl 1-[(4-nitrophenyl)Methyl] ester, (2S,4R)-
• Synonyms: 1,2-Pyrrolidinedicarboxylic acid, 4-[(Methylsulfonyl)oxy]-, 2-Methyl 1-[(4-nitrophenyl)Methyl] ester, (2S,4R)-;(2S,4R)-4-[(methylsulfonyl)oxy]-1,2-Pyrrolidinedicarboxylic acid 2-methyl 1-[(4-nitrophenyl)methyl]ester;2-O-methyl 1-O-[(4-nitrophenyl)methyl] (2S,4R)-4-methylsulfonyloxypyrrolidine-1,2-dicarboxylate;(2S,4R)-2-Methyl 1-(4-nitrobenzyl) 4-((methylsulfonyl)oxy)pyrrolidine-1,2-dicarboxylate
• CAS NO: 138324-82-0
• Molecular Formula: C₁₅H₁₈N₂O₉S
• Molecular Weight: 402.37642
• Mol File: 138324-82-0.mol

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 1,2-Pyrrolidinedicarboxylic acid, 4-[(Methylsulfonyl)oxy]-, 2-Methyl 1-[(4-nitrophenyl)Methyl] ester, (2S,4R)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-Pyrrolidinedicarboxylic acid, 4-[(Methylsulfonyl)oxy]-, 2-Methyl 1-[(4-nitrophenyl)Methyl] ester, (2S,4R)-(138324-82-0)
• EPA Substance Registry System: 1,2-Pyrrolidinedicarboxylic acid, 4-[(Methylsulfonyl)oxy]-, 2-Methyl 1-[(4-nitrophenyl)Methyl] ester, (2S,4R)-(138324-82-0)

Safety Data

• Hazardous Substances Data: 138324-82-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1,2-Pyrrolidinedicarboxylic acid, 4-[(Methylsulfonyl)oxy]-, 2-Methyl 1-[(4-nitrophenyl)Methyl] ester, (2S,4R)is used as a pharmaceutical intermediate for the synthesis of various drugs. Its unique structure and functional groups make it a valuable building block in the development of new therapeutic agents.
Used in Chemical Research:
In the field of chemical research, 1,2-Pyrrolidinedicarboxylic acid, 4-[(Methylsulfonyl)oxy]-, 2-Methyl 1-[(4-nitrophenyl)Methyl] ester, (2S,4R)serves as a key compound for studying the properties and reactivity of complex organic molecules. Its distinct spatial configuration and functional groups allow researchers to explore new reaction pathways and mechanisms.
Used in Material Science:
1,2-Pyrrolidinedicarboxylic acid, 4-[(Methylsulfonyl)oxy]-, 2-Methyl 1-[(4-nitrophenyl)Methyl] ester, (2S,4R)is employed in material science as a component in the design and synthesis of novel materials with specific properties. Its unique structure and functional groups can contribute to the development of advanced materials with applications in various industries, such as electronics, coatings, and adhesives.

Upstream product

• 4457-32-3 4-nitrobenzyl chloroformate 
• 96034-57-0 (2S,4R)-4-Hydroxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine-2-carboxylic acid 
• 51-35-4 4R-4-hydroxyproline 
• 40216-83-9 L-4-hydroxyproline methyl ester hydrochloride 
• 124-63-0 methanesulfonyl chloride 
• 101803-29-6 (2S,4R)-4-hydroxy-2-methoxycarbonyl-1-(4-nitrobenzyloxycarbonyl)pyrrolidine 

Downstream Products

• 127626-37-3 (2S,4R)-2-hydroxymethyl-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine 
• 147117-72-4 (2S,4S)-1-p-nitrobenzyloxycarbonyl-4-tritylthiopyrrolidine-2-carboxylic acid methyl ester 
• 491878-06-9 (2S,4S)-4-acetylthio-2-[[N-aminosulfonyl-N-(tert-butyloxycarbonyl)amino]methyl]pyrrolidine-1-carboxylic acid p-nitrobenzyl ester 
• 96034-97-8 (2S,4S)-4-acetylthio-2-methoxycarbonyl-1-p-nitrobenzyloxycarbonylpyrrolidine 
• 230964-57-5 p-nitrobenzyl (1R,5S,6S)-6-<(1R)-1-hydroxyethyl>-2-<(5S,7S)-2,2,3-trimethyl-4-oxo-1,3-diazabicyclo<3.3.0>octan-7-ylthio>-1-methylcarbapen-2-em-3-carboxylate 
• 101803-42-3 (2S,4S)-4-mercapto-2-hydroxymethyl-1-(4-nitrobenzyloxycarbonyl)pyrrolidine 

Relevant articles and documents

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

Synthesis and?antibacterial activities of?new 1β-methylcarbapenems having aminopyrimidinylthioether moiety

The synthesis of new 1β-methylcarbapenems 1a-d bearing aminopyrimidinylthioether moiety at C-5 position of pyrrolidine ring and their antibacterial activities are described. All the compounds exhibited potent antibacterial activity. Of these carbapenems, 1d showed the best combination of antibacterial activity and stability to dehydropeptidase-I (DHP-I).

Practical large-scale synthesis of the 2-aminomethylpyrrolidin-4-ylthio-containing side chain of the novel carbapenem antibiotic doripenem

The first synthesis using an original procedure and a practical large-scale process using an improved procedure for the synthesis of the N-PNZ-protected 2-aminomethylpyrrolidin-4-ylthio-containing side chain of doripenem hydrate (S-4661), a novel parenteral 1β-methylcarbapenem antibiotic, are described, trans-4-Hydroxy-L-proline (4) was converted in an efficient process to (2S,4S)-4-acetylthio-2-(N-sulfamoyl-tert-butoxycarbonylaminomethyl) -1-(4-nitrobenzyloxycarbonyl)pyrrolidine (3) in 55-56% overall yield via a six-step sequence, which includes the two alternative routes to intermediate 13. This process requires no chromatographic purifications, no cryogenic temperatures, no haloalkane solvents, and short operating times and is amenable to a multikilogram-scale preparation. Several kilograms of the side chain 3 were successfully prepared by this process.

Synthesis and antibacterial activity of 1β-methylcarbapenem having a 1,3-diazabicyclo[3.3.0]octan-4-one moiety, Part II

The synthesis of a new series of 1β-methylcarbapenems having a 1,3- diazabicyclo[3.3.0]octan-4-one moiety is described. Their in vitro antibacterial activities against both Gram-positive and Gram-negative bacteria are tested and the effect of substituent on the bicyclic ring was investigated. A particular compound (11h) having aminoethyl group showed the most potent antibacterial activity.

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.

Aminooxypyrrolidinylthiocarbapenem compounds

An antibacterial aminooxypyrrolidinylthiocarbapenem I, its production from the corresponding carbapenem V and thiol VI, its pharmaceutical formulation, and its use or combating bacteria are presented. STR1 (wherein R is optionally substituted amino; Rsup