51693-17-5

Basic information

• Product Name: (S)-(+)-5-(Hydroxymethyl)-2-pyrrolidinone p-toluenesulfonate
• Synonyms: (S)-(+)-5-(HYDROXYMETHYL)-2-PYRROLIDINONE P-TOLUENESULFONATE;(S)-5-HYDROXYMETHYL-2-PYRROLIDINONE P-TOLUENESULFONATE;(-)-L-PYROGLUTAMOL P-TOLUENESULFONATE;(S)-(+)-5-(hydroxymethyl)-2-pyrrolidinone P-tolu;TOLUENE-4-SULFONIC ACID (S)-5-OXO-PYRROLIDIN-2-YLMETHYL ESTER;>98%ee;(S)-(+)-5-(HYDROXYMETHYL)-2-PYRROLIDINONE P-TOLUENESULFONATE 95%;(R)-(5-OXOPYRROLIDIN-2-YL)METHYL 4-METHYLBENZENESULFONATE
• CAS NO: 51693-17-5
• Molecular Formula: C₁₂H₁₅NO₄S
• Molecular Weight: 269.32
• Product Categories: Chiral Building Blocks;Heterocyclic Building Blocks;Pyrrolidines
• Mol File: 51693-17-5.mol
• Article Data: 49

Chemical Properties

• Melting Point: 124-128 °C(lit.)
• Boiling Point: 504.8 °C at 760 mmHg
• Flash Point: 259.1 °C
• Appearance: Colorless to beige/Powder
• Density: 1.275 g/cm³
• Vapor Pressure: 2.58E-10mmHg at 25°C
• Refractive Index: 1.545
• Storage Temp.: Refrigerator (+4°C)
• PKA: 15.34±0.40(Predicted)
• CAS DataBase Reference: (S)-(+)-5-(Hydroxymethyl)-2-pyrrolidinone p-toluenesulfonate(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(+)-5-(Hydroxymethyl)-2-pyrrolidinone p-toluenesulfonate(51693-17-5)
• EPA Substance Registry System: (S)-(+)-5-(Hydroxymethyl)-2-pyrrolidinone p-toluenesulfonate(51693-17-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 51693-17-5(Hazardous Substances Data)

Usage

Description

(S)-(+)-5-(Hydroxymethyl)-2-pyrrolidinone p-toluenesulfonate is a colorless to beige powder that serves as a crucial building block in the synthesis of various organic compounds, including (R)and (S)-diaminovaleric acids and 5-azasemicorrin bidentate nitrogen ligands for enantioselective catalysis. Its unique chemical structure and properties make it a valuable component in the development of new pharmaceuticals and catalysts.

Uses

Used in Pharmaceutical Synthesis:
(S)-(+)-5-(Hydroxymethyl)-2-pyrrolidinone p-toluenesulfonate is used as a building block for the synthesis of (R)and (S)-diaminovaleric acids, which are essential components in the development of various pharmaceuticals. These diamines play a significant role in the creation of drugs targeting specific medical conditions, making this compound a vital part of the pharmaceutical industry.
Used in Enantioselective Catalysis:
In the field of enantioselective catalysis, (S)-(+)-5-(Hydroxymethyl)-2-pyrrolidinone p-toluenesulfonate is used as a key component in the synthesis of 5-azasemicorrin bidentate nitrogen ligands. These ligands are crucial for the development of enantioselective catalysts, which are essential in producing chiral compounds with high selectivity and purity. This application is particularly important in the synthesis of pharmaceuticals, agrochemicals, and fine chemicals, where the enantiomeric purity of the product is critical.
Used in Chemical Research and Development:
(S)-(+)-5-(Hydroxymethyl)-2-pyrrolidinone p-toluenesulfonate is also utilized in chemical research and development, where its unique properties and reactivity are explored for the creation of new compounds and materials. Its versatility as a building block allows researchers to design and synthesize novel molecules with potential applications in various industries, including pharmaceuticals, materials science, and environmental science.

InChI:InChI=1/C12H15NO4S/c1-9-2-5-11(6-3-9)18(15,16)17-8-10-4-7-12(14)13-10/h2-3,5-6,10H,4,7-8H2,1H3,(H,13,14)/t10-/m0/s1

Upstream product

• 98-59-9 p-toluenesulfonyl chloride 
• 17342-08-4 (S)-Pyroglutaminol 
• 7149-65-7 ethyl (S)-pyroglutamate 
• 32503-27-8 tetra(n-butyl)ammonium hydrogensulfate 
• 98-79-3 L-Pyroglutamic acid 
• 56-86-0 L-glutamic acid 
• 4931-66-2 methyl (S)-pyroglutamate 

Downstream Products

• 98334-22-6 (S)-1-acetyl-5-iodomethyl-pyrrolidin-2-one 
• 72479-06-2 2-[(2S)-5-oxopyrrolidin-2-yl]acetonitrile 
• 1038924-61-6 (S)-5-biphenyl-4-ylmethylpyrrolidin-2-one 
• 1187464-85-2 N-[(2Z)-5-tert-butyl-3-{[(2S)-5-oxopyrrolidin-2-yl]methyl}-1,3-thiazol-2(3H)-ylidene]-5-chloro-2-methoxybenzamide 
• 1187465-75-3 (S,Z)-N-(5-tert-butyl-3-((5-oxopyrrolidin-2-yl)methyl)-1,3,4-thiadiazol-2(3H)-ylidene)-2-fluoro-5-(trifluoromethyl)benzamide 
• 67217-85-0 (-)-indolizidine 223AB 
• 188015-49-8 (S)-2-Methoxy-5-(toluene-4-sulfonyloxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 188015-47-6 (S)-2-Hydroxy-5-(toluene-4-sulfonyloxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 202532-13-6 N-[(S)-1-(2-{3-[(S)-3-(tert-Butyl-dimethyl-silanyloxy)-1-(2-methylsulfanyl-ethyl)-propyl]-thioureido}-ethyl)-4-(tert-butyl-diphenyl-silanyloxy)-butyl]-4-methyl-benzenesulfonamide 

Relevant articles and documents

Synthesis of N-aminomethylpyrrolidin-2-ones

Pyrrolidin-2-ones react with formaldehyde and chlorotrimethylsilane to give 1-chloromethylpyrrolidin-2-ones which upon subsequent reaction with primary and secondary amines give 1-aminomethylpyrrolidin-2-ones in good yield.

Photoredox-Catalyzed Synthesis of α-Amino Acid Amides by Imine Carbamoylation

An operationally simple protocol for the photocatalytic carbamoylation of imines is reported. Easily available, bench-stable 4-amido Hantzsch ester derivatives serve as precursors to carbamoyl radicals that undergo rapid addition to N-aryl imines. The reaction proceeds under blue light irradiation in the presence of the photocatalyst 3DPAFIPN and Br?nsted/Lewis acid additives. Mechanistic studies indicated a photoredox mechanism that involves carbamoyl radicals.

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