Diethyl 2,2'-(2,5-dimethyl-3,6-dioxopiperazine-1,4-diyl)bis(4-phenylbutanoate)

Base Information

• Chemical Name: Diethyl 2,2'-(2,5-dimethyl-3,6-dioxopiperazine-1,4-diyl)bis(4-phenylbutanoate)
• CAS No.: 151387-05-2
• Molecular Formula: C₃₀H₃₈N₂O₆
• Molecular Weight: 522.642
• UNII: ZAU3Z2124E
• Wikidata: Q27295238
• Mol file: 151387-05-2.mol

Synonyms:151387-05-2;Ramipril impurity O [EP];ZAU3Z2124E;UNII-ZAU3Z2124E;Diethyl 2,2'-(2,5-dimethyl-3,6-dioxopiperazine-1,4-diyl)bis(4-phenylbutanoate);ethyl (2S)-2-[(2S,5S)-4-[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]-2,5-dimethyl-3,6-dioxopiperazin-1-yl]-4-phenylbutanoate;(alpha1S,alpha4S,2S,5S)-2,5-Dimethyl-3,6-dioxo-alpha1,alpha4-bis(2-phenylethyl)-1,4-piperazinediacetic Acid 1,4-Diet;1,4-Piperazinediacetic acid, 2,5-dimethyl-3,6-dioxo-alpha1,alpha4-bis(2-phenylethyl)-, 1,4-diethyl ester, (alpha1S,alpha4S,2S,5S)-;RAMIPRIL IMPURITY O [EP IMPURITY];Q27295238;1,4-PIPERAZINEDIACETIC ACID, 2,5-DIMETHYL-3,6-DIOXO-.ALPHA.1,.ALPHA.4-BIS(2-PHENYLETHYL)-, 1,4-DIETHYL ESTER, (.ALPHA.1S,.ALPHA.4S,2S,5S)-

Chemical Property of Diethyl 2,2'-(2,5-dimethyl-3,6-dioxopiperazine-1,4-diyl)bis(4-phenylbutanoate)

Chemical Property:

• Melting Point: 109 - 111oC
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility.: Acetonitrile (Slightly), Chloroform (Slightly)
• XLogP3: 5.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 14
• Exact Mass: 522.27298694
• Heavy Atom Count: 38
• Complexity: 739

Purity/Quality:

99% ^*data from raw suppliers

(α1S,α4S,2S,5S)-2,5-Dimethyl-3,6-dioxo-α1,α4-bis(2-phenylethyl)-1,4-piperazinediaceticAcid1,4-DiethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCOC(=O)C(CCC1=CC=CC=C1)N2C(C(=O)N(C(C2=O)C)C(CCC3=CC=CC=C3)C(=O)OCC)C
• Isomeric SMILES: CCOC(=O)[C@H](CCC1=CC=CC=C1)N2[C@H](C(=O)N([C@H](C2=O)C)[C@@H](CCC3=CC=CC=C3)C(=O)OCC)C
• Uses: (α1S,α4S,2S,5S)-2,5-Dimethyl-3,6-dioxo-α1,α4-bis(2-phenylethyl)-1,4-piperazinediacetic Acid 1,4-Diethyl Ester is an impurity of Ramipril (R111000), an antihypertensive agent that exerts inhibitory activities towards the angiotensin converting enzyme (ACE).

Technology Process of Diethyl 2,2'-(2,5-dimethyl-3,6-dioxopiperazine-1,4-diyl)bis(4-phenylbutanoate)

There total 1 articles about Diethyl 2,2'-(2,5-dimethyl-3,6-dioxopiperazine-1,4-diyl)bis(4-phenylbutanoate) 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: 76.6%

[1(S)-(ethoxycarbonyl)-3-phenylpropyl]-(S)-alanine (82717-96-2,122076-80-6) → N,N'-bis<1'-(S)-1-carboethoxy-3'-phenylpropyl>-3,6-(S)-dimethyl-2,5-diketopiperazine (151387-05-2)

Guidance literature:

With dmap; di-tert-butyl dicarbonate; triethylamine; In dichloromethane; for 10h; Ambient temperature;

upstream raw materials:

[1(S)-(ethoxycarbonyl)-3-phenylpropyl]-(S)-alanine

Refernces