Ladarixin

Base Information

• Chemical Name: Ladarixin
• CAS No.: 849776-05-2
• Molecular Formula: C11H12F3NO6S2
• Molecular Weight: 375.347
• UNII: DEH7Q6472O
• ChEMBL ID: CHEMBL189475
• DSSTox Substance ID: DTXSID50234030
• NCI Thesaurus Code: C170087
• Pharos Ligand ID: ADYHMNDM4ZZF
• Wikidata: Q27276351
• Mol file: 849776-05-2.mol

Synonyms:2'-((4'-trifluoromethanesulfonyloxy)phenyl)-N-methanesulfonylpropionamide;DF 2156A;DF 2156Y;DF-2156A;DF-2156Y;DF2156A;DF2156Y;ladarixin

Chemical Property of Ladarixin

Chemical Property:

• XLogP3: 2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 5
• Exact Mass: 375.00581394
• Heavy Atom Count: 23
• Complexity: 624

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C1=CC=C(C=C1)OS(=O)(=O)C(F)(F)F)C(=O)NS(=O)(=O)C
• Isomeric SMILES: C[C@H](C1=CC=C(C=C1)OS(=O)(=O)C(F)(F)F)C(=O)NS(=O)(=O)C
• Recent ClinicalTrials: A Single Dose Study About the Influence of Food on the Oral Bioavailability of Ladarixin Capsule in Healthy Volunteers
• Recent EU Clinical Trials: A phase 2, multicentre, randomized, double-blind, placebo-controlled study to assess the efficacy and safety of 400 mg twice a day oral ladarixin in patients with new-onset type 1 diabetes

Technology Process of Ladarixin

There total 5 articles about Ladarixin 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: 79.0%

methanesulfonamide (3144-09-0) → Meraxin (849776-05-2)

Guidance literature:

(R)-(-)-2-(4-trifluoromethanesulfonyloxy)phenylpropionic acid; In dichloromethane; at 20 ℃; for 1.5h;

methanesulfonamide; With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 20 ℃;

Reference yield: 79.0%

(R)-(-)-2-(4-trifluoromethanesulfonyloxy)phenylpropionic acid (533931-60-1) + methanesulfonamide (3144-09-0) → Meraxin (849776-05-2)

Guidance literature:

(R)-(-)-2-(4-trifluoromethanesulfonyloxy)phenylpropionic acid; With 1,1'-carbonyldiimidazole; In dichloromethane; at 20 ℃; for 1.5h;

methanesulfonamide; With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 20 ℃; for 16h;

DOI:10.1021/jm049227l

Reference yield:

(R)-2-(4-hydroxyphenyl)propionic acid methyl ester (533931-57-6) → Meraxin (849776-05-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 95 percent / N,N-diisopropylamine / CH₂Cl₂ / 3 h / 20 °C

2.1: 83 percent / aq. HCl; glacial acetic acid / 3 h / Heating

3.1: 1,1'-carbonyldiimidazole / CH₂Cl₂ / 1.5 h / 20 °C

3.2: 79 percent / DBU / CH₂Cl₂ / 16 h / 20 °C

With hydrogenchloride; acetic acid; diisopropylamine; 1,1'-carbonyldiimidazole; In dichloromethane;

DOI:10.1021/jm049227l

upstream raw materials:

(R)-(-)-2-(4-trifluoromethanesulfonyloxy)phenylpropionic acid

methanesulfonamide

(R)-2-(4-hydroxyphenyl)propionic acid methyl ester

(R)-2-(4-trifluoromethanesulfonyloxyphenyl)propionic acid methyl ester