(2E,4E,6E)-N-[(1S)-3-[[(2S)-3-methyl-1-[(3S,4R)-4-methyl-2,5-dioxopyrrolidin-3-yl]-1-oxobutan-2-yl]amino]-3-oxo-1-phenylpropyl]octa-2,4,6-trienamide

Base Information

• Chemical Name: (2E,4E,6E)-N-[(1S)-3-[[(2S)-3-methyl-1-[(3S,4R)-4-methyl-2,5-dioxopyrrolidin-3-yl]-1-oxobutan-2-yl]amino]-3-oxo-1-phenylpropyl]octa-2,4,6-trienamide
• CAS No.: 108868-95-7
• Molecular Formula: C27H33 N3 O5
• Molecular Weight: 479.58
• Wikipedia: Andrimid
• Mol file: 108868-95-7.mol

Synonyms:andrimid

Chemical Property of (2E,4E,6E)-N-[(1S)-3-[[(2S)-3-methyl-1-[(3S,4R)-4-methyl-2,5-dioxopyrrolidin-3-yl]-1-oxobutan-2-yl]amino]-3-oxo-1-phenylpropyl]octa-2,4,6-trienamide

Chemical Property:

• Vapor Pressure: 2.69E-25mmHg at 25°C
• Boiling Point: 795.4°Cat760mmHg
• PKA: 8.23±0.70(Predicted)
• Flash Point: 234.9°C
• PSA: 121.44000
• Density: 1.155g/cm³
• LogP: 3.65170
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 11
• Exact Mass: 479.24202116
• Heavy Atom Count: 35
• Complexity: 883

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC=CC=CC=CC(=O)NC(CC(=O)NC(C(C)C)C(=O)C1C(C(=O)NC1=O)C)C2=CC=CC=C2
• Isomeric SMILES: C/C=C/C=C/C=C/C(=O)N[C@@H](CC(=O)N[C@@H](C(C)C)C(=O)[C@@H]1[C@H](C(=O)NC1=O)C)C2=CC=CC=C2

Technology Process of (2E,4E,6E)-N-[(1S)-3-[[(2S)-3-methyl-1-[(3S,4R)-4-methyl-2,5-dioxopyrrolidin-3-yl]-1-oxobutan-2-yl]amino]-3-oxo-1-phenylpropyl]octa-2,4,6-trienamide

There total 25 articles about (2E,4E,6E)-N-[(1S)-3-[[(2S)-3-methyl-1-[(3S,4R)-4-methyl-2,5-dioxopyrrolidin-3-yl]-1-oxobutan-2-yl]amino]-3-oxo-1-phenylpropyl]octa-2,4,6-trienamide 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%

octatrienyl-D-β-phenylalanine (124731-96-0) + (3S)-L-valine-(4S)-methylsuccinimide (124731-95-9) → andrimid (108868-95-7)

Guidance literature:

With dmap; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; In N,N-dimethyl-formamide; at 0 ℃; for 0.0833333h;

DOI:10.1016/S0040-4039(00)92179-8

Reference yield:

L-malic acid (2174-58-5) → andrimid (108868-95-7)

Guidance literature:

Multi-step reaction with 7 steps

1.1: acetyl chloride / 60 °C

2.1: N,N'-carbonyldiimidazole / CH₂Cl₂ / 0 - 45 °C

3.1: N,N'-carbonyldiimidazole / tetrahydrofuran

3.2: lithium hexamethyldisilazide / tetrahydrofuran / -65 °C

4.1: H₂ / Pd/C / ethanol

5.1: 2'-bromoacetophenone; triethylamine / acetonitrile

6.1: HCl / dioxane

7.1: O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium*PF₆; i-Pr₂EtN / CH₂Cl₂; dimethylformamide

With hydrogenchloride; 2-bromophenyl methyl ketone; hydrogen; triethylamine; N-ethyl-N,N-diisopropylamine; acetyl chloride; HATU; 1,1'-carbonyldiimidazole; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/j.bmcl.2004.12.002

Reference yield:

(3S)-Boc-L-valine-(4S)-methyl-N-O-benzylsuccinimide (182007-77-8) → andrimid (108868-95-7)

Guidance literature:

Multi-step reaction with 4 steps

1: H₂ / Pd/C / ethanol

2: 2'-bromoacetophenone; triethylamine / acetonitrile

3: HCl / dioxane

4: O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium*PF₆; i-Pr₂EtN / CH₂Cl₂; dimethylformamide

With hydrogenchloride; 2-bromophenyl methyl ketone; hydrogen; triethylamine; N-ethyl-N,N-diisopropylamine; HATU; palladium on activated charcoal; In 1,4-dioxane; ethanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/j.bmcl.2004.12.002

upstream raw materials:

octatrienyl-D-β-phenylalanine

(3S)-L-valine-(4S)-methylsuccinimide

(3S)-β-phenylalanine-L-valine-(4S)-methylsuccinimide

(2E,4E,6E)-octa-2,4,6-trienoic acid