Fosinoprilat

Base Information

• Chemical Name: Fosinoprilat
• CAS No.: 95399-71-6
• Molecular Formula: C23H34NO5P
• Molecular Weight: 435.5
• Hs Code.: 2933995300
• UNII: S312EY6ZT8
• DSSTox Substance ID: DTXSID80869253
• Nikkaji Number: J261.896F
• Wikidata: Q27077720
• NCI Thesaurus Code: C65762
• RXCUI: 1546393
• Pharos Ligand ID: H92XWZUHKVYZ
• Metabolomics Workbench ID: 66891
• ChEMBL ID: CHEMBL581
• Mol file: 95399-71-6.mol

Synonyms:fosfenopril;fosinoprilat;fosinoprilic acid;SQ 27519;SQ-27,519;SQ-27519

Chemical Property of Fosinoprilat

Chemical Property:

• Vapor Pressure: 2.64E-22mmHg at 25°C
• Melting Point: >300 °C
• Refractive Index: 1.564
• Boiling Point: 728.9 °C at 760 mmHg
• PKA: 2.75±0.50(Predicted)
• Flash Point: 394.6 °C
• PSA: 104.72000
• Density: 1.238 g/cm³
• LogP: 4.09960
• Storage Temp.: -20°C Freezer
• Solubility.: Methanol (Slightly), Water (Slightly)
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 9
• Exact Mass: 435.21746018
• Heavy Atom Count: 30
• Complexity: 627

Purity/Quality:

98%Min ^*data from raw suppliers

FosinoprilatDisodiumSalt ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCC(CC1)C2CC(N(C2)C(=O)CP(=O)(CCCCC3=CC=CC=C3)O)C(=O)O
• Isomeric SMILES: C1CCC(CC1)[C@@H]2C[C@H](N(C2)C(=O)CP(=O)(CCCCC3=CC=CC=C3)O)C(=O)O
• Uses: A metabolite of Fosinopril, a phosphinic acid containing angiotensin converting enzyme (ACE) inhibitor Fosinoprilat (Fosinopril EP Impurity A) is a metabolite of Fosinopril (F727800), a phosphinic acid containing angiotensin converting enzyme (ACE) inhibitor.

Technology Process of Fosinoprilat

There total 4 articles about Fosinoprilat 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:

(2S,4S)-4-Cyclohexyl-1-{2-[ethoxy-(4-phenyl-butyl)-phosphinoyl]-acetyl}-pyrrolidine-2-carboxylic acid → Fosinoprilat (95399-71-6)

Guidance literature:

With trimethylsilyl bromide; In dichloromethane;

DOI:10.1021/jm00401a014

Reference yield:

[Ethoxy-(4-phenylbutyl)phosphinyl]acetic acid (83623-46-5) → Fosinoprilat (95399-71-6)

Guidance literature:

Multi-step reaction with 2 steps

1: carbonyldiimidazole, Et₃N / acetonitrile / 48 h / Ambient temperature

2: bromotrimethylsilane / CH₂Cl₂

With trimethylsilyl bromide; triethylamine; 1,1'-carbonyldiimidazole; In dichloromethane; acetonitrile;

DOI:10.1021/jm00401a014

Reference yield:

(2S,4S)-4-cyclohexylpyrrolidine-2-carboxylic acid (103201-78-1,130092-20-5) → Fosinoprilat (95399-71-6)

Guidance literature:

Multi-step reaction with 2 steps

1: carbonyldiimidazole, Et₃N / acetonitrile / 48 h / Ambient temperature

2: bromotrimethylsilane / CH₂Cl₂

With trimethylsilyl bromide; triethylamine; 1,1'-carbonyldiimidazole; In dichloromethane; acetonitrile;

DOI:10.1021/jm00401a014

upstream raw materials:

[Ethoxy-(4-phenylbutyl)phosphinyl]acetic acid

(2S,4S)-4-cyclohexylpyrrolidine-2-carboxylic acid

Refernces

• 1、 Krapcho,Turk,Cushman,Powell,DeForrest,Spitzmiller,Karanewsky,Duggan,Rovnvak,Schwartz,Natarajan,Godfrey,Ryono,Neubeck,Atwa,Petrillo Jr.. "Angiotensin-converting enzyme inhibitors. Mercaptan, carboxyalkyl dipeptide, and phosphinic acid inhibitors incorporating 4-substituted prolines". . p. 1148 - 1160. Retrieved 2007/10/02.