bis(p-nitrobenzyl) 6-[N-(p-nitrobenzyloxycarbonyl)glycyl-L-α-aminopimelyl]aminopenicillanate

Base Information

• Chemical Name: bis(p-nitrobenzyl) 6-[N-(p-nitrobenzyloxycarbonyl)glycyl-L-α-aminopimelyl]aminopenicillanate
• CAS No.: 726201-89-4
• Molecular Formula: C₃₉H₄₁N₇O₁₅S
• Molecular Weight: 879.858
• Mol file: 726201-89-4.mol

Synonyms:bis(p-nitrobenzyl) 6-[N-(p-nitrobenzyloxycarbonyl)glycyl-L-α-aminopimelyl]aminopenicillanate

Chemical Property of bis(p-nitrobenzyl) 6-[N-(p-nitrobenzyloxycarbonyl)glycyl-L-α-aminopimelyl]aminopenicillanate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of bis(p-nitrobenzyl) 6-[N-(p-nitrobenzyloxycarbonyl)glycyl-L-α-aminopimelyl]aminopenicillanate

There total 6 articles about bis(p-nitrobenzyl) 6-[N-(p-nitrobenzyloxycarbonyl)glycyl-L-α-aminopimelyl]aminopenicillanate 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: 40.0%

6-aminopenicillanic acid p-nitrobenzyl ester (29750-72-9) + p-nitrobenzyl N-(p-nitrobenzyloxycarbonyl)glycyl-L-α-aminopimelate (726201-88-3) → bis(p-nitrobenzyl) 6-[N-(p-nitrobenzyloxycarbonyl)glycyl-L-α-aminopimelyl]aminopenicillanate (726201-89-4)

Guidance literature:

With benzotriazol-1-ol; dicyclohexyl-carbodiimide; In N,N-dimethyl-formamide; at 20 ℃; for 3h;

DOI:10.1021/ja048850s

Reference yield:

1-bromomethyl-4-nitro-benzene (100-11-8) → bis(p-nitrobenzyl) 6-[N-(p-nitrobenzyloxycarbonyl)glycyl-L-α-aminopimelyl]aminopenicillanate (726201-89-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: Et₃N / acetone / 0.5 h / 0 °C

1.2: 0.04 g / acetone / 4 h / 0 °C

2.1: 40 percent / 1-hydroxybenzotriazole; dicyclohexylcarbodiimide / dimethylformamide / 3 h / 20 °C

With benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; In N,N-dimethyl-formamide; acetone;

DOI:10.1021/ja048850s

Reference yield:

N-[[(4-Nitrophenyl)methoxy]carbonyl]glycine (4596-53-6) → bis(p-nitrobenzyl) 6-[N-(p-nitrobenzyloxycarbonyl)glycyl-L-α-aminopimelyl]aminopenicillanate (726201-89-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 37 percent / EDC / dimethylformamide / 24 h / 4 °C

2.1: 70 percent / aq. NaHCO₃ / 1,2-dimethoxy-ethane / 7 h / 20 °C

3.1: dicyclohexylamine / dimethylformamide / 0.08 h / 75 - 85 °C

3.2: 72 percent / dimethylformamide / 75 - 80 °C

4.1: 40 percent / 1-hydroxybenzotriazole; dicyclohexylcarbodiimide / dimethylformamide / 3 h / 20 °C

With sodium hydrogencarbonate; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-cyclohexyl-cyclohexanamine; dicyclohexyl-carbodiimide; In 1,2-dimethoxyethane; N,N-dimethyl-formamide;

DOI:10.1021/ja048850s

upstream raw materials:

6-aminopenicillanic acid p-nitrobenzyl ester

p-nitrobenzyl N-(p-nitrobenzyloxycarbonyl)glycyl-L-α-aminopimelate

N-[[(4-Nitrophenyl)methoxy]carbonyl]glycine

1-bromomethyl-4-nitro-benzene