N2-1[(1S)-Ethoxycarbonyl-3-phenylpropyl]-N6-trifluoroacetyl-L-lysyl-L-proline

Base Information

• Chemical Name: N2-1[(1S)-Ethoxycarbonyl-3-phenylpropyl]-N6-trifluoroacetyl-L-lysyl-L-proline
• CAS No.: 103300-91-0
• Molecular Formula: C25H34F3N3O6
• Molecular Weight: 529.557
• European Community (EC) Number: 600-416-8
• Mol file: 103300-91-0.mol

Synonyms:103300-91-0;1-[2-[(1-ethoxy-1-oxo-4-phenylbutan-2-yl)amino]-6-[(2,2,2-trifluoroacetyl)amino]hexanoyl]pyrrolidine-2-carboxylic acid;N2-1[(1S)-Ethoxycarbonyl-3-phenylpropyl]-N6-trifluoroacetyl-L-lysyl-L-proline;WEPXGLCNGPXOQG-UHFFFAOYSA-N;NS00114764

Chemical Property of N2-1[(1S)-Ethoxycarbonyl-3-phenylpropyl]-N6-trifluoroacetyl-L-lysyl-L-proline

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 78 °C
• Refractive Index: 1.519
• Boiling Point: 714.798 °C at 760 mmHg
• PKA: 3.13±0.20(Predicted)
• Flash Point: 386.096 °C
• PSA: 125.04000
• Density: 1.269 g/cm³
• LogP: 3.15320
• Storage Temp.: 2-8°C
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 15
• Exact Mass: 529.23997030
• Heavy Atom Count: 37
• Complexity: 773

Purity/Quality:

99% ^*data from raw suppliers

N2-(1-(S)-Ethoxycarbonyl-3-phenylpropyl)-n6-trifluoroacetyl-L-lysine-L-proline ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C(CCC1=CC=CC=C1)NC(CCCCNC(=O)C(F)(F)F)C(=O)N2CCCC2C(=O)O
• Uses: N2-(1-(S)-Ethoxycarbonyl-3-phenylpropyl)-n6-t rifluoroacetyl-L-lysine-L-proline is used as a reactant in the synthesis of Lisinopril, an angiotensin converting enzyme (ACE) inhibitor.

Technology Process of N2-1[(1S)-Ethoxycarbonyl-3-phenylpropyl]-N6-trifluoroacetyl-L-lysyl-L-proline

There total 2 articles about N2-1[(1S)-Ethoxycarbonyl-3-phenylpropyl]-N6-trifluoroacetyl-L-lysyl-L-proline 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:

L-proline (147-85-3,25191-13-3,37159-97-0,4305-67-3,4607-28-7) + N2-[1-(S)-ethoxycarbonyl-3-phenylpropyl]-N6-trifluoroacetyl-L-lysine (116169-90-5) → Nε-(trifluoroacetyl)-Nα-<(S)-1-(ethoxycarbonyl)-3-phenylpropyl>-L-lysyl-L-proline (103300-91-0)

Guidance literature:

L-proline; With tetrabutylammonium carbonate; In ethanol; at 50 - 60 ℃; for 0.166667h;

N₂-[1-(S)-ethoxycarbonyl-3-phenylpropyl]-N₆-trifluoroacetyl-L-lysine; With 1-hydroxy-pyrrolidine-2,5-dione; dicyclohexyl-carbodiimide; In tetrahydrofuran; at 0 - 30 ℃; for 9h; Reagent/catalyst; Temperature;

Reference yield:

2-oxo-4-phenylbutanoic acid ethyl ester (64920-29-2) + Nε-(trifluoroacetyl)-L-lysyl-L-proline (103300-89-6) → Nε-(trifluoroacetyl)-Nα-<(R)-1-(ethoxycarbonyl)-3-phenylpropyl>-L-lysyl-L-proline (112246-14-7) + Nε-(trifluoroacetyl)-Nα-<(S)-1-(ethoxycarbonyl)-3-phenylpropyl>-L-lysyl-L-proline (103300-91-0)

Guidance literature:

nickel; Product distribution; var. catalysts and reducing agents, diastereomeric ratio;

DOI:10.1021/jo00239a029

Reference yield: 92.0%

Nε-(trifluoroacetyl)-Nα-<(S)-1-(ethoxycarbonyl)-3-phenylpropyl>-L-lysyl-L-proline (103300-91-0) → Lisinopril (76547-98-3)

Guidance literature:

With water; sodium hydroxide; at 40 - 45 ℃; pH=12 - 13;

upstream raw materials:

2-oxo-4-phenylbutanoic acid ethyl ester

N^ε-(trifluoroacetyl)-L-lysyl-L-proline

L-proline

N₂-[1-(S)-ethoxycarbonyl-3-phenylpropyl]-N₆-trifluoroacetyl-L-lysine

Downstream raw materials:

Lisinopril

lisinopril

Refernces

• 1、 Blacklock,Shuman,Butcher,Shearin Jr.,Budavari,Grenda. "Synthesis of semisynthetic dipeptides using N-carboxyanhydrides and chiral induction on Raney nickel. A method practical for large scale". . p. 836 - 844. Retrieved 2007/10/02.