rac Ambrisentan Methyl Ester

Base Information

• Chemical Name: rac Ambrisentan Methyl Ester
• CAS No.: 1240470-84-1
• Molecular Formula: C23H24N2O4
• Molecular Weight: 392.45
• DSSTox Substance ID: DTXSID40442925
• Mol file: 1240470-84-1.mol

Synonyms:rac Ambrisentan Methyl Ester;1240470-84-1;rac Ambrisentan-d3 Methyl Ester;1329837-75-3;methyl 2-(4,6-dimethylpyrimidin-2-yl)oxy-3-methoxy-3,3-diphenylpropanoate;AGN-PC-07RIXJ;SCHEMBL2352546;DTXSID40442925;(S)-Methyl 2-((4,6-dimethylpyrimidin-2-yl)-oxy)-3-methoxy-3,3-diphenylpropanoate;CS-T-47594;SB49870;FT-0661547

Chemical Property of rac Ambrisentan Methyl Ester

Chemical Property:

• Boiling Point: 553.9±60.0 °C(Predicted)
• PKA: 1.93±0.30(Predicted)
• PSA: 70.54000
• Density: 1.177±0.06 g/cm3(Predicted)
• LogP: 3.60400
• XLogP3: 4.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 8
• Exact Mass: 392.17360725
• Heavy Atom Count: 29
• Complexity: 489

Purity/Quality:

97% ^*data from raw suppliers

racAmbrisentanMethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=NC(=N1)OC(C(=O)OC)C(C2=CC=CC=C2)(C3=CC=CC=C3)OC)C
• Uses: Protected Ambrisentan.

Technology Process of rac Ambrisentan Methyl Ester

There total 18 articles about rac Ambrisentan Methyl Ester 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: 96.0%

ambrisentan (177036-94-1) + methyl iodide (74-88-4) → (S)-2-[(4,6-dimethylpyrimidin-2-yl)oxy]-3-methoxy-3,3-diphenylpropionic acid methyl ester (1106685-61-3,1240470-84-1)

Guidance literature:

ambrisentan; With potassium carbonate; In acetone; for 0.5h;

methyl iodide; In acetone; for 3h;

Reference yield: 94.0%

2-hydroxy-3-methoxy-3,3-diphenylpropionicacid methyl ester (178306-47-3) + 4,6-dimethyl-2-methylsulfonylpyrimidine (35144-22-0) → (S)-methyl-2-(4,6-dimethylpyrimidin-2-yloxy)-3-methoxy-3,3-diphenylpropionate (1240470-84-1)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; for 8h; Solvent; Reagent/catalyst; Inert atmosphere;

DOI:10.1021/acs.oprd.8b00184

Reference yield: 81.0%

ambrisentan (177036-94-1) + diazomethyl-trimethyl-silane (18107-18-1) → (S)-2-[(4,6-dimethylpyrimidin-2-yl)oxy]-3-methoxy-3,3-diphenylpropionic acid methyl ester (1106685-61-3,1240470-84-1)

Guidance literature:

In tetrahydrofuran; methanol; hexane; at 20 ℃; for 0.5h;

DOI:10.1021/jo201927m

upstream raw materials:

2-hydroxy-3-methoxy-3,3-diphenylpropionicacid methyl ester

4,6-dimethyl-2-methylsulfonylpyrimidine

benzophenone

3,3-diphenyloxirane-2-carboxylic acid methyl ester

Downstream raw materials:

ambrisentan

(+)-(2S)-2-[(4,6-dimethylpyrimidin-2-yl)oxy]-3-methoxy-3,3-diphenylpropanoic acid dicyclohexylamine salt

4,6-dimethyl-2(1H)-pyrimidinone

ambrisentan

Refernces

• 1、 Feng, Wei-Dong,Zhuo, Song-Ming,Yu, Jun,Zhao, Chuan-Meng,Zhang, Fu-Li. "Process Research for (+)-Ambrisentan, an Endothelin-A Receptor Antagonist". . p. 1200 - 1207. Retrieved 2018/09/06.
• 2、 -. "PROCESS FOR THE PREPARATION OF AN ENDOTHELIN RECEPTOR ANTAGONIST". Page/Page column 21-22. . Retrieved 2013/05/09.