diallyl 4-{[2'-(N,N-bis(2''-mesyloxyethyl)amino)phenyl]carbamoyloxymethyl}phenylcarbamoyl-L-glutamate

Base Information

• Chemical Name: diallyl 4-{[2'-(N,N-bis(2''-mesyloxyethyl)amino)phenyl]carbamoyloxymethyl}phenylcarbamoyl-L-glutamate
• CAS No.: 528837-09-4
• Molecular Formula: C₃₂H₄₂N₄O₁₃S₂
• Molecular Weight: 754.836
• Mol file: 528837-09-4.mol

Synonyms:diallyl 4-{[2'-(N,N-bis(2''-mesyloxyethyl)amino)phenyl]carbamoyloxymethyl}phenylcarbamoyl-L-glutamate

Chemical Property of diallyl 4-{[2'-(N,N-bis(2''-mesyloxyethyl)amino)phenyl]carbamoyloxymethyl}phenylcarbamoyl-L-glutamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of diallyl 4-{[2'-(N,N-bis(2''-mesyloxyethyl)amino)phenyl]carbamoyloxymethyl}phenylcarbamoyl-L-glutamate

There total 6 articles about diallyl 4-{[2'-(N,N-bis(2''-mesyloxyethyl)amino)phenyl]carbamoyloxymethyl}phenylcarbamoyl-L-glutamate 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: 57.0%

diallyl 4-{[2'-(N,N-bis(2''-hydroxyethyl)amino)phenyl]carbamoyloxymethyl}phenylcarbamoyl-L-glutamate (528837-04-9) + Methanesulfonic anhydride (7143-01-3) → diallyl 4-{[2'-(N,N-bis(2''-mesyloxyethyl)amino)phenyl]carbamoyloxymethyl}phenylcarbamoyl-L-glutamate (528837-09-4)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 20 ℃;

DOI:10.1021/jm020462i

Reference yield:

N,N-bis(2-hydroxyethyl)-2-nitroaniline (7334-82-9) → diallyl 4-{[2'-(N,N-bis(2''-mesyloxyethyl)amino)phenyl]carbamoyloxymethyl}phenylcarbamoyl-L-glutamate (528837-09-4)

Guidance literature:

Multi-step reaction with 6 steps

1: 95.1 percent / imidazole / dimethylformamide / 20 °C

2: 99 percent / H₂ / Pd/C / tetrahydrofuran

3: Et₃N / CH₂Cl₂

4: 1.99 g / dibutyltin laurate / CH₂Cl₂ / 20 °C

5: 63.5 percent / triethylamine trihydrofluoride / tetrahydrofuran / 20 °C

6: 57 percent / 4-(N,N-dimethyl)aminopyridine; Et₃N / CH₂Cl₂ / 20 °C

With 1H-imidazole; dmap; dibutyltin(II) dilaurate; triethylamine trihydrofluoride; hydrogen; triethylamine; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm020462i

Reference yield:

2-nitro-N,N-bis[2'-(tert-butyldimethylsilyloxy)ethyl]aniline (528836-34-2) → diallyl 4-{[2'-(N,N-bis(2''-mesyloxyethyl)amino)phenyl]carbamoyloxymethyl}phenylcarbamoyl-L-glutamate (528837-09-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 99 percent / H₂ / Pd/C / tetrahydrofuran

2: Et₃N / CH₂Cl₂

3: 1.99 g / dibutyltin laurate / CH₂Cl₂ / 20 °C

4: 63.5 percent / triethylamine trihydrofluoride / tetrahydrofuran / 20 °C

5: 57 percent / 4-(N,N-dimethyl)aminopyridine; Et₃N / CH₂Cl₂ / 20 °C

With dmap; dibutyltin(II) dilaurate; triethylamine trihydrofluoride; hydrogen; triethylamine; palladium on activated charcoal; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jm020462i

upstream raw materials:

diallyl 4-{[2'-(N,N-bis(2''-hydroxyethyl)amino)phenyl]carbamoyloxymethyl}phenylcarbamoyl-L-glutamate

Methanesulfonic anhydride

N,N-bis(2-hydroxyethyl)-2-nitroaniline

2-nitro-N,N-bis[2'-(tert-butyldimethylsilyloxy)ethyl]aniline

Downstream raw materials:

diallyl 4-{[2'-(N,N-bis(2''-chloroethyl)amino)phenyl]carbamoyloxymethyl}phenylcarbamoyl-L-glutamate

diallyl 4-{[2'-(N,N-bis(2''-bromoethyl)amino)phenyl]carbamoyloxymethyl}phenylcarbamoyl-L-glutamate

diallyl 4-{[2'-(N,N-bis(2''-iodoethyl)amino)phenyl]carbamoyloxymethyl}phenylcarbamoyl-L-glutamate