(2S,3S,4R)-4-(1,3-benzodioxol-5-yl)-1-[2-(dibutylamino)-2-oxoethyl]-2-(4-methoxyphenyl)pyrrolidine-3-carboxylic acid

Base Information

• Chemical Name: (2S,3S,4R)-4-(1,3-benzodioxol-5-yl)-1-[2-(dibutylamino)-2-oxoethyl]-2-(4-methoxyphenyl)pyrrolidine-3-carboxylic acid
• CAS No.: 173937-91-2
• Molecular Formula: C29H38N2O6
• Molecular Weight: 510.631
• DSSTox Substance ID: DTXSID40870204
• Nikkaji Number: J739.355E
• Pharos Ligand ID: 9L454S1CMQKY
• ChEMBL ID: CHEMBL428504
• Mol file: 173937-91-2.mol

Synonyms:(11C)ABT-627;2-(4-methoxyphenyl)-4-(1,3-benzodioxol-5-yl)-1-(((dibutylamino)carbonyl)methyl)pyrrolidine-3-carboxylic acid;A 127722;A 127722.5;A 147627;A-127722;A-127722.5;A-147627;A127722;A127722.5;A147627;ABT 627;ABT-627;ABT627;atrasentan;Atrasentan Hydrochloride;Xinlay

Chemical Property of (2S,3S,4R)-4-(1,3-benzodioxol-5-yl)-1-[2-(dibutylamino)-2-oxoethyl]-2-(4-methoxyphenyl)pyrrolidine-3-carboxylic acid

Chemical Property:

• Vapor Pressure: 2.76E-18mmHg at 25°C
• Melting Point: 122-124°
• Boiling Point: 659.4 °C at 760 mmHg
• PKA: 3.49±0.60(Predicted)
• Flash Point: 352.6 °C
• PSA: 88.54000
• Density: 1.188 g/cm³
• LogP: 4.63190
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 12
• Exact Mass: 510.27298694
• Heavy Atom Count: 37
• Complexity: 734

Purity/Quality:

98%min ^*data from raw suppliers

Atrasentan ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCN(CCCC)C(=O)CN1CC(C(C1C2=CC=C(C=C2)OC)C(=O)O)C3=CC4=C(C=C3)OCO4
• Isomeric SMILES: CCCCN(CCCC)C(=O)CN1C[C@H]([C@@H]([C@H]1C2=CC=C(C=C2)OC)C(=O)O)C3=CC4=C(C=C3)OCO4
• Uses: Palliative treatment of bone pain due to metastatic prostate cancer and disease progression (endothelin (ETA) receptor antagonist). Atrasentan is a selective antagonist of the endothelin-A (ETA) receptor and binds selectively to the ETA receptor, which may result in inhibition of endothelin-induced angiogenesis and tumor cell proliferation.

Technology Process of (2S,3S,4R)-4-(1,3-benzodioxol-5-yl)-1-[2-(dibutylamino)-2-oxoethyl]-2-(4-methoxyphenyl)pyrrolidine-3-carboxylic acid

There total 18 articles about (2S,3S,4R)-4-(1,3-benzodioxol-5-yl)-1-[2-(dibutylamino)-2-oxoethyl]-2-(4-methoxyphenyl)pyrrolidine-3-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: 94.0%

→ atrasentan (173937-91-2)

Guidance literature:

Reference yield: 78.0%

2-[(2R,3R,4S)-4-Benzo[1,3]dioxol-5-yl-3-((S)-4-benzyl-2-oxo-oxazolidine-3-carbonyl)-2-(4-methoxy-phenyl)-pyrrolidin-1-yl]-N,N-dibutyl-acetamide → atrasentan (173937-91-2)

Guidance literature:

With lithium hydroxide; dihydrogen peroxide; In tetrahydrofuran; for 0.5h;

DOI:10.1021/jm9505369

Reference yield:

ethyl (2R,3R,4S)-(+)-2-(4-methoxyphenyl)-4-(1,3-benzodioxol-5-yl)pyrrolidine-3-carboxylate, (S)-(+)-mandelate (195708-14-6) + N,N-dibutylbromoacetamide (40124-27-4) → atrasentan (173937-91-2)

Guidance literature:

ethyl (2R,3R,4S)-(+)-2-(4-methoxyphenyl)-4-(1,3-benzodioxol-5-yl)pyrrolidine-3-carboxylate, (S)-(+)-mandelate; With sodium hydrogencarbonate; In water; ethyl acetate; at 25 ℃;

N,N-dibutylbromoacetamide; With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 10 ℃; for 12h;

With hydrogenchloride; sodium hydroxide; more than 3 stages;

upstream raw materials:

5-((E)-2-nitroethenyl)-1,3-benzodioxole

N,N-dibutylbromoacetamide

dibutylamine

ethyl 2-(4-methoxyphenyl)-4-(1,3-benzodioxol-5-yl)-4,5-dihydro-3H-pyrrole-3-carboxylate

Downstream raw materials:

Atrasentan hydrochloride

Refernces

• 1、 -. "CRYSTALLINE FORM 1 OF ATRASENTAN HXDROCHLORIDE". Page/Page column 24. . Retrieved 2008/06/13.
• 2、 -. "Crystalline form of a drug". Page/Page column 9. . Retrieved 2010/10/20.