Enrasentan

Base Information

• Chemical Name: Enrasentan
• CAS No.: 167256-08-8
• Molecular Formula: C₂₉H₃₀O₈
• Molecular Weight: 506.552
• UNII: QG16H8A6ZH
• DSSTox Substance ID: DTXSID50168260
• Nikkaji Number: J732.584C
• Wikidata: Q27287239
• NCI Thesaurus Code: C87727
• Pharos Ligand ID: 6AYRV1J2VLRK
• Metabolomics Workbench ID: 149791
• ChEMBL ID: CHEMBL431651
• Mol file: 167256-08-8.mol

Synonyms:(1S,2R,3S)-3-(2-(2-Hydroxyethoxy)-4-methoxyphenyl)-1-(3,4- (methylenedioxy)phenyl)-5-propoxy-2-indancarboxylic acid;3-(2-(2-hydroxyeth-1-yloxy)-4-methoxyphenyl)-1-(3,4-methylenedioxyphenyl)-5-(prop-1-yloxy)indan-2-carboxylic acid;enrasentan;SB 217242;SB-217242

Chemical Property of Enrasentan

Chemical Property:

• Vapor Pressure: 1.11E-19mmHg at 25°C
• Boiling Point: 684.6°Cat760mmHg
• Flash Point: 226.1°C
• Density: 1.3g/cm³
• XLogP3: 4.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 10
• Exact Mass: 506.19406791
• Heavy Atom Count: 37
• Complexity: 747

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCOC1=CC2=C(C=C1)C(C(C2C3=C(C=C(C=C3)OC)OCCO)C(=O)O)C4=CC5=C(C=C4)OCO5
• Isomeric SMILES: CCCOC1=CC2=C(C=C1)[C@@H]([C@H]([C@@H]2C3=C(C=C(C=C3)OC)OCCO)C(=O)O)C4=CC5=C(C=C4)OCO5

Technology Process of Enrasentan

There total 16 articles about Enrasentan 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: 81.0%

LiOH-H2 O + water (7732-18-5) + [1S-(1α,2α,3α)]-methyl 1-(1,3-benzodioxol-5-yl)-2,3-dihydro-3-[2-(2-hydroxyethoxy)-4-methoxyphenyl]-5-propoxy-1H-indene-2-carboxylate (190965-53-8) → (1S,2R,3S)-3-[2-(2-Hydroxyeth-1-yloxy)-4-methoxyphenyl]-1-(3,4-methylenedioxyphenyl)-5-(prop-1-yloxy)indane-2-carboxylic acid (167256-08-8)

Guidance literature:

In tetrahydrofuran; methanol; ethyl acetate;

Reference yield:

[1S-(1α,2α,3α)]-methyl 1-(1,3-benzodioxol-5-yl)-2,3-dihydro-3-[2-(2-hydroxyethoxy)-4-methoxyphenyl]-5-propoxy-1H-indene-2-carboxylate (190965-53-8) → hemiethylenediamine salt + enrasentan (167256-08-8)

Guidance literature:

With sodium hydroxide; In methanol; water; isopropyl alcohol;

Reference yield:

[1S-(1α,2α,3α)]-methyl 1-(1,3-benzodioxol-5-yl)-2,3-dihydro-3-[2-(2-hydroxyethoxy)-4-methoxyphenyl]-5-propoxy-1H-indene-2-carboxylate (190965-53-8) → (1S,2R,3S)-3-[2-(2-Hydroxyeth-1-yloxy)-4-methoxyphenyl]-1-(3,4-methylenedioxyphenyl)-5-(prop-1-yloxy)indane-2-carboxylic acid (167256-08-8)

Guidance literature:

With sodium hydroxide; In methanol; water; isopropyl alcohol;

upstream raw materials:

[1S-(1α,2α,3α)]-methyl 1-(1,3-benzodioxol-5-yl)-2,3-dihydro-3-[2-(2-hydroxyethoxy)-4-methoxyphenyl]-5-propoxy-1H-indene-2-carboxylate

piperonal

1-(2-Bromo-5-propoxyphenyl)ethanone

3-(1,3-benzodioxol-5-yl)-6-propoxy-1H-inden-1-one

Refernces

• 1、 -. "Stereoselective synthesis of endothelin receptor antagonists". . . Retrieved 2008/06/13.
• 2、 Clark, William M.,Tickner-Eldridge, Ann M.,Kris Huang,Pridgen, Lendon N.,Olsen, Mark A.,Mills, Robert J.,Lantos, Ivan,Baine, Neil H.. "A catalytic enantioselective synthesis of the endothelin receptor antagonists SB-209670 and SB-217242. A base-catalyzed stereospecific formal 1,3-hydrogen transfer of a chiral 3-arylindenol". . p. 4550 - 4551. Retrieved 2007/10/03.