4-Methyl hydrogen N-[2-cyano-4-[(1,1-dimethylethoxy)carbonyl]phenyl]-L-aspartate

Base Information

• Chemical Name: 4-Methyl hydrogen N-[2-cyano-4-[(1,1-dimethylethoxy)carbonyl]phenyl]-L-aspartate
• CAS No.: 171050-08-1
• Molecular Formula: C₁₇H₂₀N₂O₆
• Molecular Weight: 348.356
• DSSTox Substance ID: DTXSID301133819
• Nikkaji Number: J835.878H
• Mol file: 171050-08-1.mol

Synonyms:SCHEMBL6656640;DTXSID301133819;171050-08-1;4-Methyl hydrogen N-[2-cyano-4-[(1,1-dimethylethoxy)carbonyl]phenyl]-L-aspartate

Chemical Property of 4-Methyl hydrogen N-[2-cyano-4-[(1,1-dimethylethoxy)carbonyl]phenyl]-L-aspartate

Chemical Property:

• XLogP3: 2.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 9
• Exact Mass: 348.13213636
• Heavy Atom Count: 25
• Complexity: 559

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)C1=CC(=C(C=C1)NC(CC(=O)OC)C(=O)O)C#N
• Isomeric SMILES: CC(C)(C)OC(=O)C1=CC(=C(C=C1)N[C@@H](CC(=O)OC)C(=O)O)C#N

Technology Process of 4-Methyl hydrogen N-[2-cyano-4-[(1,1-dimethylethoxy)carbonyl]phenyl]-L-aspartate

There total 4 articles about 4-Methyl hydrogen N-[2-cyano-4-[(1,1-dimethylethoxy)carbonyl]phenyl]-L-aspartate 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%

D-aspartic acid β-methyl ester hydrochloride + t-butyl 4-fluoro-3-cyanobenzoate (171050-07-0) → N-[[2-cyano-4-t-butoxycarbonyl]phenyl]-L-aspartic acid β-methyl ester (171050-08-1)

Guidance literature:

With sodium hydrogencarbonate; dimethyl sulfoxide; In water;

Reference yield: 75.0%

β-methyl L-aspartate (2177-62-0) + t-butyl 4-fluoro-3-cyanobenzoate (171050-07-0) → N-[[2-cyano-4-t-butoxycarbonyl]phenyl]-L-aspartic acid β-methyl ester (171050-08-1)

Guidance literature:

With sodium hydrogencarbonate; In water; dimethyl sulfoxide; at 72 ℃; for 24h;

DOI:10.1016/S0040-4039(97)00570-4

Reference yield:

5-Bromo-2-fluoro-benzonitrile (179897-89-3) → N-[[2-cyano-4-t-butoxycarbonyl]phenyl]-L-aspartic acid β-methyl ester (171050-08-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 52 percent / dppf, KOAc / Pd(OAc)2 / dimethylsulfoxide

2: 72 percent / 5 molpercent TfOH / diethyl ether / -78 °C / to RT, sealed pressure bottle

3: 75 percent / NaHCO₃ / dimethylsulfoxide; H₂O / 24 h / 72 °C

With 1,1'-bis-(diphenylphosphino)ferrocene; trifluorormethanesulfonic acid; potassium acetate; sodium hydrogencarbonate; palladium diacetate; In diethyl ether; water; dimethyl sulfoxide;

DOI:10.1016/S0040-4039(97)00570-4

upstream raw materials:

β-methyl L-aspartate

t-butyl 4-fluoro-3-cyanobenzoate

5-Bromo-2-fluoro-benzonitrile

3-cyano-4-fluorobenzoic acid

Downstream raw materials:

N-[[2-formyl-4-t-butoxycarbonyl]phenyl]-L-aspartic acid β-methyl ester