20275-18-7

Basic information

• Product Name: 4-HYDROXY-1-(TOLUENE-4-SULFONYL)-PYRROLIDINE-2-CARBOXYLIC ACID
• Synonyms: AKOS 90624;4-HYDROXY-1-(TOLUENE-4-SULFONYL)-PYRROLIDINE-2-CARBOXYLIC ACID;4-HYDROXY-1-[(4-METHYLPHENYL)SULFONYL]-2-PYRROLIDINECARBOXYLIC ACID;TIMTEC-BB SBB012252
• CAS NO: 20275-18-7
• Molecular Formula: C₁₂H₁₅NO₅S
• Molecular Weight: 285.32
• Mol File: 20275-18-7.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 522.5°Cat760mmHg
• Flash Point: 269.8°C
• Appearance: /
• Density: 1.481g/cm³
• Vapor Pressure: 9.63E-12mmHg at 25°C
• CAS DataBase Reference: 4-HYDROXY-1-(TOLUENE-4-SULFONYL)-PYRROLIDINE-2-CARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 4-HYDROXY-1-(TOLUENE-4-SULFONYL)-PYRROLIDINE-2-CARBOXYLIC ACID(20275-18-7)
• EPA Substance Registry System: 4-HYDROXY-1-(TOLUENE-4-SULFONYL)-PYRROLIDINE-2-CARBOXYLIC ACID(20275-18-7)

Safety Data

• Hazardous Substances Data: 20275-18-7(Hazardous Substances Data)

Usage

Description

4-HYDROXY-1-(TOLUENE-4-SULFONYL)-PYRROLIDINE-2-CARBOXYLIC ACID is a chemical compound with a molecular formula C16H19NO5S. It is a derivative of pyrrolidine and carboxylic acid, featuring a hydroxyl group and a toluene-4-sulfonyl moiety attached to the pyrrolidine ring. 4-HYDROXY-1-(TOLUENE-4-SULFONYL)-PYRROLIDINE-2-CARBOXYLIC ACID possesses important structural features, including the toluene-4-sulfonyl group, which serves as a protecting group for amines in organic synthesis, and the carboxylic acid functionality, which can participate in various chemical reactions. The presence of a hydroxyl group also allows for further functionalization of the molecule. These characteristics make 4-HYDROXY-1-(TOLUENE-4-SULFONYL)-PYRROLIDINE-2-CARBOXYLIC ACID a valuable intermediate for the synthesis of various compounds with potential biological activities.

Uses

Used in Pharmaceutical Industry:
4-HYDROXY-1-(TOLUENE-4-SULFONYL)-PYRROLIDINE-2-CARBOXYLIC ACID is used as a building block in the synthesis of complex molecules for pharmaceutical applications. Its unique structural features, including the toluene-4-sulfonyl group, carboxylic acid functionality, and hydroxyl group, enable the development of compounds with potential biological activities, making it a promising candidate for the creation of new drugs.
Used in Organic Synthesis:
In the field of organic synthesis, 4-HYDROXY-1-(TOLUENE-4-SULFONYL)-PYRROLIDINE-2-CARBOXYLIC ACID is used as a protecting group for amines. The toluene-4-sulfonyl group can be easily introduced and removed during the synthesis process, allowing chemists to control the reactivity of amine groups and facilitate the synthesis of complex organic molecules.
Used in Chemical Reactions:
4-HYDROXY-1-(TOLUENE-4-SULFONYL)-PYRROLIDINE-2-CARBOXYLIC ACID is used as a reactant in various chemical reactions due to its carboxylic acid functionality. The carboxylic acid group can participate in reactions such as esterification, amide formation, and other condensation reactions, making it a versatile building block for the synthesis of a wide range of compounds.
Used in Functionalization of Molecules:
The presence of a hydroxyl group in 4-HYDROXY-1-(TOLUENE-4-SULFONYL)-PYRROLIDINE-2-CARBOXYLIC ACID allows for further functionalization of the molecule. This hydroxyl group can be converted into various functional groups, such as ethers, esters, or other derivatives, expanding the range of applications and properties of the synthesized compounds.

InChI:InChI=1/C12H15NO5S/c1-8-2-4-10(5-3-8)19(17,18)13-7-9(14)6-11(13)12(15)16/h2-5,9,11,14H,6-7H2,1H3,(H,15,16)/p-1/t9-,11-/m1/s1

Upstream product

• 98-59-9 p-toluenesulfonyl chloride 
• 51-35-4 4R-4-hydroxyproline 

Downstream Products

• 127641-07-0 (1S,4S)-N-Benzyl-2,5-diazabicyclo-[2.2.1]heptane 
• 5234-72-0 (1S,4S)-5-Benzyl-2-tosyl-2,5-diazabicyclo<2.2.1>heptane 
• 125109-57-1 (2S,4R)-1-(4-Tolylsulfonyl)-2-(chloromethyl)-4-((4-tolylsulfonyl)oxy)pyrrolidine 
• 125109-58-2 (1S,4S)-2-(4-Tolylsulfonyl)-5-methyl-2,5-diazabicyclo<2.2.1>heptane 
• 114086-15-6 (1S,4S)-2-Methyl-2,5-diazabicyclo<2.2.1>heptane Dihydrobromide 
• 5234-75-3 (2S,4R)-1-(4-tolylsulfonyl)-4-<(4-tolylsulfonyl)oxy>-2-<<(4-tolylsulfonyl)oxy>methyl>pyrrolidine 
• 79767-59-2 (2S)-methyl 1-(4-methylphenylsulfonyl)-3,4-dihydropyrrole-2-carboxylate 
• 16257-73-1 N,O-ditosyl-trans-4-hydroxy-L-proline methyl ester 
• 20275-13-2 methyl (2S,4S)-4-azido-1-(p-tolylsulfonyl)pyrrolidine-2-carboxylate 
• 81519-89-3 methyl (2S,4S)-4-amino-1-(p-tolylsulfonyl)pyrrolidine-2-carboxylate 
• 16257-57-1 methyl (2S,4R)-4-hydroxy-1-(p-tolylsulfonyl)pyrrolidine-2-carboxylate 
• 57850-05-2 (2S,4R)-2-Hydroxymethyl-4-hydroxy-1-(4-toluenesulfonyl)-pyrrolidine 
• 16257-65-1 5-aza-5-(p-toluenosulfonyl)-2-oxa-3-oxo-bicyclo<2.2.1>heptane 

Relevant articles and documents

Design, synthesis, and electrophysiological evaluation of NS6740 derivatives: Exploration of the structure-activity relationship for alpha7 nicotinic acetylcholine receptor silent activation

The α7 nicotinic acetylcholine receptor (nAChR) silent agonists, able to induce receptor desensitization and promote the α7 metabotropic function, are emerging as new promising therapeutic anti-inflammatory agents. Herein, we report the structure–activity

Synthesis of novel derivatives of (1S,4S)-2,5-diazabicyclo[2.2.1]heptane and their evaluation as potential ligands in asymmetric catalysis

Thirty-seven (most of them novel) chiral derivatives of (1S,4S)-2,5-diazabicyclo[2.2.1]heptane (2-36, 38, 39) were prepared from (S)-trans-4-hydroxyproline. A selection of these chiral ligands were examined as potential ligands in the preparation of catalysts for the enantioselective addition of diethylzinc to aldehydes and as chiral Lewis acid activators in the asymmetric Diels-Alder reaction. In the former system, diamine 30 induced up to 92 % enantiomeric excess in the formation of (S)-phenyl ethyl carbinol, whereas in the case of the cycloaddition reaction between cyclopentadiene and 3-acryloyloxazolidin-2-one the catalytic complex formed between dimeric derivative 8 and copper triflate [Cu(OTf)2] afforded the expected product in a 95:5 endo/exo ratio and up to 72 % ee for the major diastereomeric product. Finally, some of the novel chiral diamines prepared in this work were also evaluated as potential organocatalysts in the asymmetric amination of ethyl α-phenyl-α-cyano acetate. Bifunctional derivative 12 provided the animated product in excellent yield and with up to 40 % ee. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.

Trans-4-aminoproline, a phytotoxic metabolite with herbicidal activity produced by Ascochyta caulina

A phytotoxic metabolite, characterized through NMR techniques and synthetic methods as trans-4-aminoproline, was isolated from the culture filtrates of Ascochyta caulina, a promising mycoherbicide for biological control of Chenopodium album. The metabolite, which shows interesting phytotoxic properties, together with ascaulitoxin (recently characterized as N2-β-D-glucoside of the unusual bis-amino acid 2,4,7-triamino-5- hydroxyoctandioc acid) and another unidentified compound, compose an active fraction of A. caulina culture filtrates with promising herbicidal properties. When assayed on leaves of host and non host dicots, including wild and cultivated plants, the trans-4-aminoproline showed a wide range of toxicity, with leaves of C. album being the most sensitive. Other interesting aspects were its inefficacy on several monocots, both cultivated and wild, and its lack of antifungal, antibiotic and zootoxic activities. This is the first report on trans-4-aminoproline as naturally occurring compound and phytotoxic metabolite produced by A. caulina. (C) 2000 Elsevier Science Ltd.