Rovatirelin

Base Information

• Chemical Name: Rovatirelin
• CAS No.: 204386-76-5
• Molecular Formula: C16H22N4O4S
• Molecular Weight: 366.44
• UNII: 9DL0X410PY
• DSSTox Substance ID: DTXSID90174385
• Nikkaji Number: J3.663.192I
• NCI Thesaurus Code: C152262
• Metabolomics Workbench ID: 155428
• ChEMBL ID: CHEMBL4297622
• Mol file: 204386-76-5.mol

Synonyms:(1-(((5-methyl-2-oxooxazolidin-4-yl)carbonyl)-3-(thiazol-4-yl)alanyl)-2-methylpyrrolidine;rovatirelin

Chemical Property of Rovatirelin

Chemical Property:

• Boiling Point: 755.1±60.0 °C(Predicted)
• PKA: 11.03±0.60(Predicted)
• PSA: 135.85000
• Density: 1.315±0.06 g/cm3(Predicted)
• LogP: 1.09640
• XLogP3: 1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 366.13617637
• Heavy Atom Count: 25
• Complexity: 546

Purity/Quality:

>98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CCCN1C(=O)C(CC2=CSC=N2)NC(=O)C3C(OC(=O)N3)C
• Isomeric SMILES: C[C@@H]1CCCN1C(=O)[C@H](CC2=CSC=N2)NC(=O)[C@@H]3[C@@H](OC(=O)N3)C
• Recent ClinicalTrials: A Confirmatory Study of KPS-0373 in Patients With Spinocerebellar Degeneration (SCD)

Technology Process of Rovatirelin

There total 14 articles about Rovatirelin 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: 57.0%

(R)-(+)-2-methylpyrrolidine p-toluenesulfonate (204387-55-3) + (2S)-2-[(4S,5S)-5-methyl-2-oxooxazolidine-4-carboxamido]-3-(thiazol-4-yl)propanoic acid → rovatirelin (204386-76-5)

Guidance literature:

(2S)-2-[(4S,5S)-5-methyl-2-oxooxazolidine-4-carboxamido]-3-(thiazol-4-yl)propanoic acid; With 1-hydroxy-pyrrolidine-2,5-dione; dicyclohexyl-carbodiimide; In tetrahydrofuran; N,N-dimethyl-formamide; at 0 ℃; for 4h;

(R)-(+)-2-methylpyrrolidine p-toluenesulfonate; With triethylamine; In tetrahydrofuran; N,N-dimethyl-formamide; at 0 - 20 ℃; for 25h;

DOI:10.1002/psc.3228

Reference yield:

1-N-[(4S,5S)-(5-methyl-2-oxooxazolidin-4-yl)carbonyl]-3-(thiazol-4-yl)-L-alanyl-(2R)-2-methylpyrrolidine trihydrate → rovatirelin (204386-76-5)

Guidance literature:

at 100 ℃; for 14h;

Reference yield:

1-N-[(4S,5S)-(5-methyl-2-oxooxazolidin-4-yl)carbonyl]-3-(thiazol-4-yl)-L-alanyl-(2R)-2-methylpyrrolidine monohydrate → rovatirelin (204386-76-5)

Guidance literature:

at 100 ℃; for 15h;

upstream raw materials:

benzhydryl (2S)-2-amino-3-(thiazol-4-yl)propanoate p-toluenesulfonate

(2S)-2-amino-3-(thiazol-4-yl)propanoic acid

(2S)-2-amino-3-(thiazol-4-yl)propanoic acid p-toluenesulfonate

2-(R)-methylpyrrolidine-1-carboxylic acid tert-butyl ester

Refernces

• 1、 -. "A PHARMACEUTICAL COMPOSITION FOR TREATING ATAXIA, MULTIPLE SYSTEM ATROPHY OR BALANCE DISORDERS". Page/Page column 10. . Retrieved 2008/06/13.