(2S,4S)-4-cyclohexyl-1-[2-[[(1S)-2-methyl-1-(1-oxopropoxy)propoxy]-(4-phenylbutyl)phosphoryl]-1-oxoethyl]-2-pyrrolidinecarboxylic acid

Base Information

• Chemical Name: (2S,4S)-4-cyclohexyl-1-[2-[[(1S)-2-methyl-1-(1-oxopropoxy)propoxy]-(4-phenylbutyl)phosphoryl]-1-oxoethyl]-2-pyrrolidinecarboxylic acid
• CAS No.: 98048-97-6
• Molecular Formula: C₃₀H₄₆NO₇P
• Molecular Weight: 563.672
• Hs Code.: 2942000000
• ChEMBL ID: CHEMBL1886787
• NCI Thesaurus Code: C65761
• Nikkaji Number: J261.844C
• RXCUI: 50166
• Wikidata: Q27165624
• Wikipedia: Fosinopril
• Mol file: 98048-97-6.mol

Synonyms:Dynacil;Fosenopril;Fosinil;Fosinopril;Fosinopril Sodium;Fosinopril, (1(S*(R*)),2 alpha,4 alpha)-(D-Pro)-Isomer;Fosinopril, (1(S*(R*)),2 alpha,4 beta)-Isomer;Fosinopril, (1(S*(S*)),2 alpha,4 beta)-Isomer;Fosinorm;Fositens;Fozitec;Hiperlex;Monopril;Newace;Sodium, Fosinopril;SQ 28,555;SQ 28555;SQ-28,555;SQ-28555;SQ28,555;SQ28555;Staril;Tenso Stop;Tensocardil

Chemical Property of (2S,4S)-4-cyclohexyl-1-[2-[[(1S)-2-methyl-1-(1-oxopropoxy)propoxy]-(4-phenylbutyl)phosphoryl]-1-oxoethyl]-2-pyrrolidinecarboxylic acid

Chemical Property:

• Appearance/Colour: White crystal
• Vapor Pressure: 6.67E-21mmHg at 25°C
• Melting Point: 149-153 °C
• Refractive Index: 1.531
• Boiling Point: 705.7 °C at 760 mmHg
• PKA: 3.38±0.40(Predicted)
• Flash Point: 380.6 °C
• PSA: 120.02000
• Density: 1.173 g/cm³
• LogP: 6.05920
• Water Solubility.: Insoluble
• XLogP3: 6.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 15
• Exact Mass: 563.30118980
• Heavy Atom Count: 39
• Complexity: 850

Purity/Quality:

99% ^*data from raw suppliers

Fosinopril ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Angiotensin-Converting Enzyme Inhibitors
• Canonical SMILES: CCC(=O)OC(C(C)C)OP(=O)(CCCCC1=CC=CC=C1)CC(=O)N2CC(CC2C(=O)O)C3CCCCC3
• Isomeric SMILES: CCC(=O)O[C@H](C(C)C)OP(=O)(CCCCC1=CC=CC=C1)CC(=O)N2C[C@@H](C[C@H]2C(=O)O)C3CCCCC3
• Recent ClinicalTrials: Prevention of Renal and Vascular Endstage Disease Intervention Trial
• Recent EU Clinical Trials: Infertility and inflammatory urogenital diseases as a result of the metabolic syndrome
• Uses: mydriatic,

Technology Process of (2S,4S)-4-cyclohexyl-1-[2-[[(1S)-2-methyl-1-(1-oxopropoxy)propoxy]-(4-phenylbutyl)phosphoryl]-1-oxoethyl]-2-pyrrolidinecarboxylic acid

There total 8 articles about (2S,4S)-4-cyclohexyl-1-[2-[[(1S)-2-methyl-1-(1-oxopropoxy)propoxy]-(4-phenylbutyl)phosphoryl]-1-oxoethyl]-2-pyrrolidinecarboxylic 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: 57.1%

C19H29O6P (128948-00-5,123599-78-0) + (2S,4S)-4-cyclohexylpyrrolidine-2-carboxylic acid (103201-78-1,130092-20-5) → fosinopril (1356446-78-0,98048-97-6,97825-24-6)

Guidance literature:

C₁₉H₂₉O₆P; With pyridine; pivaloyl chloride; triethylamine; In dichloromethane; at -15 - -10 ℃; for 4h; Large scale;

(2S,4S)-4-cyclohexylpyrrolidine-2-carboxylic acid; In dichloromethane; at 20 - 25 ℃; for 2h; Large scale;

Reference yield:

C19H29O6P (128948-00-5,123599-78-0) + trans-4-cyclohexyl-L-proline hydrochloride (90657-55-9) → fosinopril (1356446-78-0,98048-97-6,97825-24-6)

Guidance literature:

C₁₉H₂₉O₆P; With benzotriazol-1-ol; dicyclohexyl-carbodiimide; In dichloromethane; at -18 - 20 ℃; for 4h;

(2S,4S)-4-cyclohexylpyrrolidine-2-carboxylic acid; With N-ethyl-N,N-diisopropylamine; In dichloromethane; at -18 - 20 ℃; for 24h;

Reference yield:

(2S,4S)-1-Benzoyl-4-phenyl-pyrrolidine-2-carboxylic acid (120851-71-0) → fosinopril (1356446-78-0,98048-97-6,97825-24-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: hydrogenchloride / 1,4-dioxane / 12 h / Inert atmosphere; Reflux

2.1: 5% rhodium-on-charcoal; hydrogenchloride; hydrogen / methanol / 2 h / 30 °C / 15001.5 Torr

3.1: pyridine; pivaloyl chloride; triethylamine / dichloromethane / 4 h / -15 - -10 °C / Large scale

3.2: 2 h / 20 - 25 °C / Large scale

With pyridine; hydrogenchloride; 5% rhodium-on-charcoal; hydrogen; pivaloyl chloride; triethylamine; In 1,4-dioxane; methanol; dichloromethane;

upstream raw materials:

C₁₉H₂₉O₆P

trans-4-cyclohexyl-L-proline hydrochloride

(2S,4S)-1-Benzoyl-4-phenyl-pyrrolidine-2-carboxylic acid

trans-4-phenyl-L-proline

Refernces

• 1、 -. "COMPOSITIONS AND METHODS FOR DIAGNOSING AND TREATING SALT SENSITIVITY OF BLOOD PRESSURE". . . Retrieved 2015/02/05.
• 2、 -. "PROCESS FOR THE PREPARATION OF FOSINOPRIL AND INTERMEDIATES THEREOF". Page/Page column 5. . Retrieved 2012/06/16.