Ethyl (4R)-5-[1,1'-biphenyl]-4-yl-4-[[(1,1-dimethylethoxy)carbonyl]amino]-2-methyl-2-pentenoate

Base Information

• Chemical Name: Ethyl (4R)-5-[1,1'-biphenyl]-4-yl-4-[[(1,1-dimethylethoxy)carbonyl]amino]-2-methyl-2-pentenoate
• CAS No.: 149709-59-1
• Molecular Formula: C25H31NO4
• Molecular Weight: 409.525
• DSSTox Substance ID: DTXSID301117407
• Mol file: 149709-59-1.mol

Synonyms:DTXSID301117407;Ethyl (4R)-5-[1,1'-biphenyl]-4-yl-4-[[(1,1-dimethylethoxy)carbonyl]amino]-2-methyl-2-pentenoate

Chemical Property of Ethyl (4R)-5-[1,1'-biphenyl]-4-yl-4-[[(1,1-dimethylethoxy)carbonyl]amino]-2-methyl-2-pentenoate

Chemical Property:

• Boiling Point: 562.7±50.0 °C(Predicted)
• PKA: 11.14±0.46(Predicted)
• PSA: 64.63000
• Density: 1.081±0.06 g/cm3(Predicted)
• LogP: 5.68970
• Storage Temp.: 2-8°C
• XLogP3: 5.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 10
• Exact Mass: 409.22530847
• Heavy Atom Count: 30
• Complexity: 578

Purity/Quality:

97% ^*data from raw suppliers

(R)-Ethyl5-([1,1''-biphenyl]-4-yl)-4-((tert-butoxycarbonyl)amino)-2-methylpent-2-enoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C(=CC(CC1=CC=C(C=C1)C2=CC=CC=C2)NC(=O)OC(C)(C)C)C
• Isomeric SMILES: CCOC(=O)C(=C[C@@H](CC1=CC=C(C=C1)C2=CC=CC=C2)NC(=O)OC(C)(C)C)C

Technology Process of Ethyl (4R)-5-[1,1'-biphenyl]-4-yl-4-[[(1,1-dimethylethoxy)carbonyl]amino]-2-methyl-2-pentenoate

There total 26 articles about Ethyl (4R)-5-[1,1'-biphenyl]-4-yl-4-[[(1,1-dimethylethoxy)carbonyl]amino]-2-methyl-2-pentenoate 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: 96.0%

(R)-α-<<(1,1-dimethylethoxy)carbonyl>amino><1,1'-biphenyl>-4-propanal (149709-58-0) + (carbethoxyethylidene)triphenylphosphorane (21382-82-1) → (R)-5-biphenyl-4-yl-4-tert-butoxycarbonylamino-2-methylpent-2-enoic acid ethyl ester (149709-59-1)

Guidance literature:

In tetrahydrofuran; at 50 ℃; Solvent;

Reference yield: 78.0%

(R)-α-<<(1,1-dimethylethoxy)carbonyl>amino><1,1'-biphenyl>-4-propanal (149709-58-0) + (carbethoxyethylidene)triphenylphosphorane (21382-82-1) → ethyl 5-(4-<1,1'-biphenyl>yl)-4-<<(1,1-dimethylethoxy)carbonyl>amino>-2-methyl-2-pentenoate (149709-59-1)

Guidance literature:

In dichloromethane; for 16h; Ambient temperature;

DOI:10.1021/jm00010a014

Reference yield:

methyl (R)-α-<<(1,1-dimethylethoxy)carbonyl>amino><1,1'-biphenyl>-4-propanoate (149818-98-4) + (carbethoxyethylidene)triphenylphosphorane (21382-82-1) → ethyl 5-(4-<1,1'-biphenyl>yl)-4-<<(1,1-dimethylethoxy)carbonyl>amino>-2-methyl-2-pentenoate (149709-59-1)

Guidance literature:

methyl (R)-α-<<(1,1-dimethylethoxy)carbonyl>amino><1,1'-biphenyl>-4-propanoate; With diisobutylaluminium hydride; In dichloromethane; toluene; at -70 ℃; for 0.333333h; Inert atmosphere;

(carbethoxyethylidene)triphenylphosphorane; In dichloromethane; at 5 - 25 ℃; for 18h;

upstream raw materials:

(R)-α-<<(1,1-dimethylethoxy)carbonyl>amino><1,1'-biphenyl>-4-propanal

(carbethoxyethylidene)triphenylphosphorane

(2R)-3-(biphenyl-4-yl)-2-[(tert-butoxycarbonyl)amino]propanoic acid

N-(tert-butoxycarbonyl)-D-tyrosine methyl ester

Downstream raw materials:

(2E,4R)-5-{[1,1'-biphenyl]-4-yl}-4-{[(tert-butoxy)carbonyl]amino}-2-methylpent-2-enoic acid

ethyl (γS)-γ-amino-α-methyl<1,1'-biphenyl>-4-pentanoate

α-ethyl (γS)-γ-<(3-carboxy-1-oxopropyl)amino>-α-methyl<1,1'-biphenyl>-4-pentanoate

α-ethyl (αS,γS)-γ-<(3-carboxy-1-oxopropyl)amino>-α-methyl<1,1'-biphenyl>-4-pentanoate