(2S)-1-(3,5-dichlorophenyl)sulfonylpyrrolidine-2-carboxylic Acid

Base Information

• Chemical Name: (2S)-1-(3,5-dichlorophenyl)sulfonylpyrrolidine-2-carboxylic Acid
• CAS No.: 217326-48-2
• Molecular Formula: C11H11 Cl2 N O4 S
• Molecular Weight: 324.185
• DSSTox Substance ID: DTXSID40424928
• Nikkaji Number: J1.674.400J
• Wikidata: Q82237686
• ChEMBL ID: CHEMBL206946
• Mol file: 217326-48-2.mol

Synonyms:217326-48-2;N-(3,5-Dichlorobenzenesulfonyl)-L-proline;(2S)-1-(3,5-dichlorophenyl)sulfonylpyrrolidine-2-carboxylic Acid;CHEMBL206946;(S)-1-((3,5-Dichlorophenyl)sulfonyl)pyrrolidine-2-carboxylic acid;SCHEMBL3904078;DTXSID40424928;SRQOBFXQILTASR-JTQLQIEISA-N;BDBM50187226;MFCD06858482;3,5-Dichlorophenyl-sulfonyl-L-proline;AKOS025428050;N-(3,5-diChlorobenzenesulfonyl)-Proline;1-(3,5-Dichlorophenylsulfonyl)-L-proline;N-(3,5-Dichlorophenylsulfonyl)-L-proline;N-(3 5-Dichlorobenzenesulfonyl)-(L)-proline;(S)-1-(3,5-dichlorophenylsulfonyl)pyrrolidine-2-carboxylic acid

Chemical Property of (2S)-1-(3,5-dichlorophenyl)sulfonylpyrrolidine-2-carboxylic Acid

Chemical Property:

• Vapor Pressure: 6.46E-12mmHg at 25°C
• Refractive Index: 1.625
• Boiling Point: 526.6°Cat760mmHg
• Flash Point: 272.3°C
• PSA: 83.06000
• Density: 1.595g/cm³
• LogP: 3.24980
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 322.9785844
• Heavy Atom Count: 19
• Complexity: 440

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(N(C1)S(=O)(=O)C2=CC(=CC(=C2)Cl)Cl)C(=O)O
• Isomeric SMILES: C1C[C@H](N(C1)S(=O)(=O)C2=CC(=CC(=C2)Cl)Cl)C(=O)O
• General Description: N-(3,5-Dichlorobenzenesulfonyl)-L-proline is a key intermediate in the synthesis of potent VLA-4 antagonists, which exhibit high inhibitory activity (IC50 ~1 nM) and are explored for treating inflammatory diseases. Its incorporation into dipeptide analogues, particularly with substituted phenylalanine derivatives, enhances binding affinity and pharmacokinetic properties, including oral bioavailability and metabolic stability. The structural flexibility of this scaffold allows for further optimization, as demonstrated by the efficacy of 4-oxo derivatives, making it a promising candidate for therapeutic development.

Technology Process of (2S)-1-(3,5-dichlorophenyl)sulfonylpyrrolidine-2-carboxylic Acid

There total 5 articles about (2S)-1-(3,5-dichlorophenyl)sulfonylpyrrolidine-2-carboxylic Acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

1-(3,5-dichloro-benzenesulfonyl)-pyrrolidine-2-carboxylic acid tert-butyl ester (226066-04-2) → N-(3,5-dichlorobenzenesulfonyl)-2-(S)-proline (217326-48-2)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 20 ℃;

DOI:10.1016/j.bmcl.2006.11.011

Reference yield:

N-(3,5-dichlorobenzenesulphonyl)-L-proline methyl ester → N-(3,5-dichlorobenzenesulfonyl)-2-(S)-proline (217326-48-2)

Guidance literature:

With sodium hydroxide; In ethanol;

DOI:10.1021/jm060168g

Reference yield:

3,5-dichlorobenzensulfonyl chloride (705-21-5) → N-(3,5-dichlorobenzenesulfonyl)-2-(S)-proline (217326-48-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 94 percent / NEt(i-Pr)2; DMAP / CH₂Cl₂

2: 98 percent / TFA / CH₂Cl₂ / 20 °C

With dmap; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In dichloromethane;

DOI:10.1016/j.bmcl.2006.11.011

upstream raw materials:

3,5-dichlorobenzensulfonyl chloride

L-proline

1-(3,5-dichloro-benzenesulfonyl)-pyrrolidine-2-carboxylic acid tert-butyl ester

proline tert-butyl ester

Downstream raw materials:

3-(4-tert-butoxy-phenyl)-2-{[1-(3,5-dichloro-benzenesulfonyl)-pyrrolidine-2-carbonyl]-amino}-propionic acid tert-butyl ester

(S)-3-(4-tert-Butoxy-phenyl)-2-{[(S)-1-(3,5-dichloro-benzenesulfonyl)-pyrrolidine-2-carbonyl]-amino}-propionic acid methyl ester

(S)-2-{[(S)-1-(3,5-Dichloro-benzenesulfonyl)-pyrrolidine-2-carbonyl]-amino}-3-(4-hydroxy-phenyl)-propionic acid methyl ester

Refernces

Substituted N-(3,5-dichlorobenzenesulfonyl)-L-prolyl-phenylalanine analogues as potent VLA-4 antagonists

10.1016/S0960-894X(01)00821-6

The research aims to develop potent and selective VLA-4 (very late antigen-4) inhibitors with improved pharmacokinetic properties for potential use in treating inflammatory diseases such as asthma, multiple sclerosis, and rheumatoid arthritis. The study focuses on synthesizing and evaluating a series of substituted N-(3,5-dichlorobenzenesulfonyl)-L-prolyl- and α-methyl-L-prolyl-phenylalanine derivatives. Key chemicals used include N-(3,5-dichlorobenzenesulfonyl)-L-proline, various substituted phenylalanine derivatives, and thionyl chloride for the synthesis process. The compounds exhibited excellent potency (IC50 around 1 nM) and maintained activity with a wide variety of substituents on the phenylalanine ring. The study also explored the impact of replacing the central proline with α-methyl-proline to enhance stability and reduce metabolism. Pharmacokinetic studies in rats and other animals revealed that certain compounds, such as 16a, had good oral bioavailability, moderate clearance rates, and sustained plasma levels. The most potent analogues were the 4-oxo derivatives. The research concludes that these sulfonylated dipeptide derivatives show promise as VLA-4 inhibitors with favorable pharmacokinetic profiles, warranting further investigation for therapeutic applications.