5-R-Rivaroxaban

Base Information

• Chemical Name: 5-R-Rivaroxaban
• CAS No.: 865479-71-6
• Molecular Formula: C₁₉H₁₈ClN₃O₅S
• Molecular Weight: 435.888
• UNII: RJP4GEG36M
• ChEMBL ID: CHEMBL371106
• DSSTox Substance ID: DTXSID20468042
• Pharos Ligand ID: RTBPGBXG89R4
• Wikidata: Q72506815
• Mol file: 865479-71-6.mol

Synonyms:5-R-Rivaroxaban;865479-71-6;5R-Rivaroxaban;Rivaroxaban R-isomer;Rivaroxaban, (R)-;RJP4GEG36M;5-chloro-N-[[(5R)-2-oxo-3-[4-(3-oxomorpholin-4-yl)phenyl]-1,3-oxazolidin-5-yl]methyl]thiophene-2-carboxamide;2-Thiophenecarboxamide, 5-chloro-N-(((5R)-2-oxo-3-(4-(3-oxo-4-morpholinyl)phenyl)-5-oxazolidinyl)methyl)-;5-Chloro-N-(((5R)-2-oxo-3-(4-(3-oxo-4-morpholinyl)phenyl)-5-oxazolidinyl)methyl)-2-thiophenecarboxamide;ent-Rivaroxaban;(R)-Rivaroxaban (5-Chloro-N-[[(5R)-2-oxo-3-[4-(3-oxo-4-morpholinyl)phenyl]-5-oxazolidinyl]methyl]-2-thiophenecarboxamide);5-Chloro-N-({(5R)-2-oxo-3-[4-(3-oxomorpholin-4-yl)phenyl]-1,3-oxazolidin-5-yl}methyl)thiophene-2-carboxamide;5-Chloro-N-[[(5R)-2-oxo-3-[4-(3-oxo-4-morpholinyl)phenyl]-5-oxazolidinyl]methyl]-2-thiophenecarboxamide;Rivaroxaban Impurity A;5-chloro-N-{[(5R)-2-oxo-3-[4-(3-oxomorpholin-4-yl)phenyl]-1,3-oxazolidin-5-yl]methyl}thiophene-2-carboxamide;UNII-RJP4GEG36M;Rivaroxaban impurity A [EP];CHEMBL371106;SCHEMBL7721848;BDBM13001;BAY 59-7939 (Rivaroxaban);DTXSID20468042;BCP09021;AKOS025399394;CS-0730;HY-76948;RIVAROXABAN IMPURITY A [EP IMPURITY];E84662;A900028;(R)-5-Chloro-N-((2-oxo-3-(4-(3-oxomorpholino)phenyl)oxazolidin-5-yl)methyl)thiophene-2-carboxamide

Chemical Property of 5-R-Rivaroxaban

Chemical Property:

• Boiling Point: 732.6±60.0 °C(Predicted)
• PKA: 13.36±0.46(Predicted)
• PSA: 116.42000
• Density: 1.460
• LogP: 3.04080
• Storage Temp.: Refrigerator
• Solubility.: Acetonitrile (Slightly, Heated, Sonicated), DMSO (Slightly, Sonicated), Methanol
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 435.0655696
• Heavy Atom Count: 29
• Complexity: 645

Purity/Quality:

99% ^*data from raw suppliers

ent-Rivaroxaban ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1COCC(=O)N1C2=CC=C(C=C2)N3CC(OC3=O)CNC(=O)C4=CC=C(S4)Cl
• Isomeric SMILES: C1COCC(=O)N1C2=CC=C(C=C2)N3C[C@H](OC3=O)CNC(=O)C4=CC=C(S4)Cl
• Uses: ent-Rivaroxaban is the R-isomer of Rivaroxaban (R538000), which is a novel antithrombotic agent. A highly potent and selective, direct FXa inhibitor.

Technology Process of 5-R-Rivaroxaban

There total 233 articles about 5-R-Rivaroxaban 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: 97.0%

(S)-N-/3-{N-[4-(3-oxomorpholine-4-yl)phenyl]-N-(ethoxycarbonyl)amino}-2-hydroxyprop-1-yl/-5-chlorothiophene-2-carboxamide → Rivaroxaban (366789-02-8,865479-71-6)

Guidance literature:

With potassium carbonate; In methanol; at 20 ℃; for 2h;

DOI:10.1016/j.tetlet.2018.11.067

Reference yield: 96.0%

5-chlorothiophene-2-carbonyl chloride (42518-98-9) + 4-{4-[(5S)-5-(aminomethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl}morpholin-3-one methanesulfonic acid salt (1251952-62-1) → Rivaroxaban (366789-02-8,865479-71-6)

Guidance literature:

With potassium hydrogencarbonate; In ethanol; water; butanone; at 20 - 35 ℃; for 0.75h; Large scale;

DOI:10.1080/00304948.2020.1741300

Reference yield: 95.6%

5-chlorothiophene-2-carbonyl chloride (42518-98-9) + 4-{4-[(5S)-5-(aminomethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl}morpholin-3-one hydrochloride → Rivaroxaban (366789-02-8,865479-71-6)

Guidance literature:

4-{4-[(5S)-5-(aminomethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl}morpholin-3-one hydrochloride; With sodium carbonate; In water; acetone; at 8 - 12 ℃;

5-chlorothiophene-2-carbonyl chloride; In water; acetone; at 50 - 53 ℃; for 0.5h; Temperature;

upstream raw materials:

4-[4-[(5S)-5-(aminomethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl]morpholine-3-one

5-chlorothiophene-2-carbonyl chloride

2-((2S)-2-hydroxy-3-{[4-(3-oxomorpholin-4-yl)phenyl]amino}propyl)-1H-isoindole-1,3(2H)-dione

2-({(5S)-2-oxo-3-[4-(3-oxo-4-morpholinyl)phenyl]-1,3-oxazolidin-5-yl}methyl)-1H-isoindole-1,3(2H)-dione

Downstream raw materials:

2-{2-[1-(5-chlorothiophen-2-yl)-N-{4-[(5S)-5-{[(5-chlorothiophen-2-yl)formamido]methyl}-2-oxo-1,3-oxazolidin-3-yl]phenyl}formamido]ethoxy}acetic acid

Refernces

• 1、 -. "Preparation method of rivaroxaban". Paragraph 0013; 0017. . Retrieved 2021/03/24.
• 2、 -. "Oxazolidinone derivative and preparation method thereof". Paragraph 0018; 0021. . Retrieved 2020/03/05.