Glutaryl-alanyl-alanyl-prolylethylamide

Base Information

• Chemical Name: Glutaryl-alanyl-alanyl-prolylethylamide
• CAS No.: 83808-37-1
• Molecular Formula: C₁₈H₃₀N₄O₆
• Molecular Weight: 398.459
• DSSTox Substance ID: DTXSID10232693
• Wikidata: Q83113780
• Mol file: 83808-37-1.mol

Synonyms:glutaryl-Ala-Ala-Pro-NH-ET;glutaryl-alanyl-alanyl-prolylethylamide

Chemical Property of Glutaryl-alanyl-alanyl-prolylethylamide

Chemical Property:

• Vapor Pressure: 2.01E-23mmHg at 25°C
• Boiling Point: 731.7°C at 760 mmHg
• Flash Point: 396.3°C
• PSA: 155.38000
• Density: 1.219g/cm³
• LogP: 1.83660
• XLogP3: -2.7
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 10
• Exact Mass: 398.21653469
• Heavy Atom Count: 28
• Complexity: 609

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCN1CCCC1C(=O)NC(=O)C(C)NC(=O)C(C)NC(=O)CCCC(=O)O
• Isomeric SMILES: CCN1CCC[C@H]1C(=O)NC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)CCCC(=O)O

Technology Process of Glutaryl-alanyl-alanyl-prolylethylamide

There total 9 articles about Glutaryl-alanyl-alanyl-prolylethylamide 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: 91.0%

glutaric anhydride, (108-55-4) + alanyl-alanyl proline ethylamide (84914-64-7) → 4-{(S)-1-[(S)-2-((S)-2-Ethylcarbamoyl-pyrrolidin-1-yl)-1-methyl-2-oxo-ethylcarbamoyl]-ethylcarbamoyl}-butyric acid (83808-37-1)

Guidance literature:

In N,N-dimethyl-formamide; at 80 ℃;

Reference yield:

Proline Ethylamide (55446-83-8) → 4-{(S)-1-[(S)-2-((S)-2-Ethylcarbamoyl-pyrrolidin-1-yl)-1-methyl-2-oxo-ethylcarbamoyl]-ethylcarbamoyl}-butyric acid (83808-37-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 5.4 g / N,N'-Dicyclohexylcarbodiimide / dimethylformamide; tetrahydrofuran / 1 h / -5 °C / 1) -5 deg C, 1 h, 2) R_.T_., 12 h

2: 36percent HBr / acetic acid

3: 43 percent / N,N'-dicyclohexylcarbodiimide, 36percent HBr / CH₂Cl₂ / 1) 0 deg C, 2 h, 2) R_.T_., 12 h

4: 90 percent / HBr / acetic acid

5: 91 percent / dimethylformamide / 80 °C

With hydrogen bromide; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane; acetic acid; N,N-dimethyl-formamide;

Reference yield:

Benzyloxycarbonylproline Ethylamide (55446-81-6) → 4-{(S)-1-[(S)-2-((S)-2-Ethylcarbamoyl-pyrrolidin-1-yl)-1-methyl-2-oxo-ethylcarbamoyl]-ethylcarbamoyl}-butyric acid (83808-37-1)

Guidance literature:

Multi-step reaction with 6 steps

1: 5.7 g / 36percent HBr / acetic acid / 1 h

2: 5.4 g / N,N'-Dicyclohexylcarbodiimide / dimethylformamide; tetrahydrofuran / 1 h / -5 °C / 1) -5 deg C, 1 h, 2) R_.T_., 12 h

3: 36percent HBr / acetic acid

4: 43 percent / N,N'-dicyclohexylcarbodiimide, 36percent HBr / CH₂Cl₂ / 1) 0 deg C, 2 h, 2) R_.T_., 12 h

5: 90 percent / HBr / acetic acid

6: 91 percent / dimethylformamide / 80 °C

With hydrogen bromide; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane; acetic acid; N,N-dimethyl-formamide;

upstream raw materials:

glutaric anhydride,

alanyl-alanyl proline ethylamide

benzyloxycarbonyl-L-alanyl-L-alanine

benzyl ((S)-1-(((S)-1-hydrazinyl-1-oxopropan-2-yl)amino)-1-oxopropan-2-yl)carbamate

Refernces