(Z)-Eprosartan

Base Information

• Chemical Name: (Z)-Eprosartan
• CAS No.: 148674-39-9
• Molecular Formula: C₂₃H₂₄N₂O₄S
• Molecular Weight: 424.521
• UNII: LS37WUA6G9
• Nikkaji Number: J572.338H
• Mol file: 148674-39-9.mol

Synonyms:(Z)-Eprosartan;148674-39-9;4-[[2-butyl-5-[(Z)-2-carboxy-3-thiophen-2-ylprop-1-enyl]imidazol-1-yl]methyl]benzoic acid;SB 206328;Eprosartan, (Z)-;SB-206328;SCHEMBL4026;LS37WUA6G9;SCHEMBL156290;PDSP1_000577;PDSP2_000575;SC1437;SB206328;(alphaZ)-alpha-[[2-Butyl-1-[(4-carboxyphenyl)methyl]-1H-imidazol-5-yl]methylene]-2-thiophenepropanoic acid;2-THIOPHENEPROPANOIC ACID, ?-[[2-BUTYL-1-[(4-CARBOXYPHENYL)METHYL]-1H-IMIDAZOL-5-YL]METHYLENE]-, (?E)-;2-Thiophenepropanoic acid, alpha-[[2-butyl-1-[(4-carboxyphenyl)methyl]-1H-imidazol-5-yl]methylene]-, (alphaZ);2-Thiophenepropanoic acid, alpha-[[2-butyl-1-[(4-carboxyphenyl)methyl]-1H-imidazol-5-yl]methylene]-, (Z)

Chemical Property of (Z)-Eprosartan

Chemical Property:

• Boiling Point: 660.6±55.0 °C(Predicted)
• PKA: 3.10±0.37(Predicted)
• Density: 1.26±0.1 g/cm3(Predicted)
• XLogP3: 4.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 10
• Exact Mass: 424.14567842
• Heavy Atom Count: 30
• Complexity: 618

Purity/Quality:

95%+ or 98%+ ^*data from raw suppliers

(Z)-Eprosartan ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCCCC1=NC=C(N1CC2=CC=C(C=C2)C(=O)O)C=C(CC3=CC=CS3)C(=O)O
• Isomeric SMILES: CCCCC1=NC=C(N1CC2=CC=C(C=C2)C(=O)O)/C=C(/CC3=CC=CS3)\C(=O)O
• Uses: (Z)-Eprosartan is the Z-isomer of Eprosartan (E590100), as an impurity in tablets. (Z)-Eprosartan (Eprosartan USP Related Compound F) is the Z-isomer of Eprosartan (E590100), as an impurity in tablets.

Technology Process of (Z)-Eprosartan

There total 47 articles about (Z)-Eprosartan 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: 83.0%

methyl (E)-3-<2-butyl-1-<(4-carbomethoxyphenyl)methyl>imidazol-5-yl>-2-(2-thienylmethyl)-2-propenoate (133040-06-9) → eprosartan (133040-01-4,148674-39-9)

Guidance literature:

With potassium hydroxide; In ethanol;

DOI:10.1021/jm00108a043

Reference yield: 70.92%

2-n-butyl-1-[(4-carbomethoxyphenyl)methyl]-1H-imidazol-5-carboxaldehyde (133040-03-6) + 3-ethoxy-3-oxo-2-(thien-3-ylmethyl)propanoic acid (143468-96-6) → eprosartan (133040-01-4,148674-39-9)

Guidance literature:

2-n-butyl-1-[(4-carbomethoxyphenyl)methyl]-1H-imidazol-5-carboxaldehyde; 3-ethoxy-3-oxo-2-(thien-3-ylmethyl)propanoic acid; With piperidine; hydrogenchloride; In di-isopropyl ether; water; at 40 - 55 ℃; under 760.051 Torr; Heating / reflux;

With water; sodium hydroxide; In methanol; for 3h; Heating / reflux;

With hydrogenchloride; In methanol; water; at 35 - 40 ℃; pH=5.0 - 5.2;

Reference yield: 68.0%

eprosartan mesylate → eprosartan (133040-01-4,148674-39-9)

Guidance literature:

With hydrogenchloride; In water; at 20 ℃; pH=2;

DOI:10.1021/acs.cgd.6b01588

upstream raw materials:

methyl (E)-3-<2-butyl-1-<(4-carbomethoxyphenyl)methyl>imidazol-5-yl>-2-(2-thienylmethyl)-2-propenoate

4-[5-(1-Acetoxy-2-methoxycarbonyl-3-thiophen-2-yl-propyl)-2-butyl-imidazol-1-ylmethyl]-benzoic acid methyl ester

2-butyl-1H-imidazole

Methyl 4-(bromomethyl)benzoate