di-tert-butyl 4-{[2'-(N,N-(2''-mesyloxyethyl)(2''-chloroethyl)amino)phenyl]carbamoyloxymethyl}phenyloxycarbonyl-L-glutamate

Base Information

• Chemical Name: di-tert-butyl 4-{[2'-(N,N-(2''-mesyloxyethyl)(2''-chloroethyl)amino)phenyl]carbamoyloxymethyl}phenyloxycarbonyl-L-glutamate
• CAS No.: 528837-24-3
• Molecular Formula: C₃₃H₄₆ClN₃O₁₁S
• Molecular Weight: 728.261
• Mol file: 528837-24-3.mol

Synonyms:di-tert-butyl 4-{[2'-(N,N-(2''-mesyloxyethyl)(2''-chloroethyl)amino)phenyl]carbamoyloxymethyl}phenyloxycarbonyl-L-glutamate

Chemical Property of di-tert-butyl 4-{[2'-(N,N-(2''-mesyloxyethyl)(2''-chloroethyl)amino)phenyl]carbamoyloxymethyl}phenyloxycarbonyl-L-glutamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of di-tert-butyl 4-{[2'-(N,N-(2''-mesyloxyethyl)(2''-chloroethyl)amino)phenyl]carbamoyloxymethyl}phenyloxycarbonyl-L-glutamate

There total 7 articles about di-tert-butyl 4-{[2'-(N,N-(2''-mesyloxyethyl)(2''-chloroethyl)amino)phenyl]carbamoyloxymethyl}phenyloxycarbonyl-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: 50.0%

di-tert-butyl 4-{[2'-(N,N-bis(2''-mesyloxyethyl)amino)phenyl]carbamoyloxymethyl}phenyloxycarbonyl-L-glutamate (528837-10-7) → di-tert-butyl 4-{[2'-(N,N-bis(2''-chloroethyl)amino)phenyl]carbamoyloxymethyl}phenyloxycarbonyl-L-glutamate (528837-25-4) + di-tert-butyl 4-{[2'-(N,N-(2''-mesyloxyethyl)(2''-chloroethyl)amino)phenyl]carbamoyloxymethyl}phenyloxycarbonyl-L-glutamate (528837-24-3)

Guidance literature:

With sodium chloride; In acetonitrile; for 48h; Heating;

DOI:10.1021/jm020462i

Reference yield:

N,N-bis(2-hydroxyethyl)-2-nitroaniline (7334-82-9) → di-tert-butyl 4-{[2'-(N,N-(2''-mesyloxyethyl)(2''-chloroethyl)amino)phenyl]carbamoyloxymethyl}phenyloxycarbonyl-L-glutamate (528837-24-3)

Guidance literature:

Multi-step reaction with 7 steps

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

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

3: Et₃N / CH₂Cl₂

4: 0.97 g / dibutyl laurate / CH₂Cl₂ / 20 °C

5: 99 percent / triethylamine trihydrofluoride / tetrahydrofuran / 20 °C

6: 91.9 percent / 4-(N,N-dimethyl)aminopyridine; Et₃N / CH₂Cl₂ / 20 °C

7: 20.5 percent / NaCl / acetonitrile / 48 h / Heating

With 1H-imidazole; dmap; dibutyl laurate; triethylamine trihydrofluoride; hydrogen; triethylamine; sodium chloride; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jm020462i

Reference yield:

2-nitro-N,N-bis[2'-(tert-butyldimethylsilyloxy)ethyl]aniline (528836-34-2) → di-tert-butyl 4-{[2'-(N,N-(2''-mesyloxyethyl)(2''-chloroethyl)amino)phenyl]carbamoyloxymethyl}phenyloxycarbonyl-L-glutamate (528837-24-3)

Guidance literature:

Multi-step reaction with 6 steps

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

2: Et₃N / CH₂Cl₂

3: 0.97 g / dibutyl laurate / CH₂Cl₂ / 20 °C

4: 99 percent / triethylamine trihydrofluoride / tetrahydrofuran / 20 °C

5: 91.9 percent / 4-(N,N-dimethyl)aminopyridine; Et₃N / CH₂Cl₂ / 20 °C

6: 20.5 percent / NaCl / acetonitrile / 48 h / Heating

With dmap; dibutyl laurate; triethylamine trihydrofluoride; hydrogen; triethylamine; sodium chloride; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; acetonitrile;

DOI:10.1021/jm020462i

upstream raw materials:

di-tert-butyl 4-{[2'-(N,N-bis(2''-mesyloxyethyl)amino)phenyl]carbamoyloxymethyl}phenyloxycarbonyl-L-glutamate

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

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

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