(R) Lisinopril

Base Information

• Chemical Name: (R) Lisinopril
• CAS No.: 85955-59-5
• Molecular Formula: C21H31N3O5
• Molecular Weight: 405.494
• Mol file: 85955-59-5.mol

Synonyms:N2-[(1R)-1-Carboxy-3-phenylpropyl)-L-lysyl]L-proline;(R) Lisinopril;(R)-1-[N2-(1-Carboxy-3-phenylpropyl)-L-lysyl]L-proline

Chemical Property of (R) Lisinopril

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 666.441°C at 760 mmHg
• PKA: 2.18±0.10(Predicted)
• Flash Point: 356.851°C
• PSA: 132.96000
• Density: 1.252g/cm³
• LogP: 2.26430

Purity/Quality:

98%Min ^*data from raw suppliers

(R)Lisinopril ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: R,S,S-Isomer of Lisinopril (R)-Lisinopril is a R,S,S-isomer of (S)-Lisinopril (L469018), an orally active angiotensin-converting enzyme (ACE) inhibitor.

Technology Process of (R) Lisinopril

There total 6 articles about (R) Lisinopril 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: 75.0%

(S)-1-[N2-(1-carboxy-3-phenylpropyl]-L-lysyl]-L-proline (77726-95-5) → Lisinopril (76547-98-3) + lisinopril (85955-59-5)

Guidance literature:

With hydrogenchloride; In water; Resolution of racemate;

Reference yield:

Nε-(trifluoroacetyl)-Nα-<(S)-1-(ethoxycarbonyl)-3-phenylpropyl>-L-lysyl-L-proline (103300-91-0) → Lisinopril (76547-98-3) + lisinopril (85955-59-5)

Guidance literature:

With sodium hydroxide; sodium hydrogencarbonate; at 40 ℃; for 4h;

DOI:10.1021/jo00239a029

Reference yield:

2-oxo-4-phenylbutyric acid (710-11-2) + H-Lys(Boc)-Pro-OH (4583-24-8) → Lisinopril (76547-98-3) + lisinopril (85955-59-5)

Guidance literature:

With sodium hydroxide; Dowex 50 (H⁺, 50-100 mesh); sodium cyanoborohydride; Yield given. Multistep reaction. Yields of byproduct given; 1.) water, room temperature, pH 7.0;

DOI:10.1002/jps.2600740330

upstream raw materials:

2-oxo-4-phenylbutyric acid

H-Lys(Boc)-Pro-OH

N^ε-(trifluoroacetyl)-N^α-<(S)-1-(ethoxycarbonyl)-3-phenylpropyl>-L-lysyl-L-proline

L-proline benzyl ester hydrochloride

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.