N-[(p-carboxyphenyl)methyl]-N'-[(p-(N-t-BOC-aminomethyl)phenyl)methyl]-1,4,5,8-naphthalenetetracarboxylic diimide

Base Information

• Chemical Name: N-[(p-carboxyphenyl)methyl]-N'-[(p-(N-t-BOC-aminomethyl)phenyl)methyl]-1,4,5,8-naphthalenetetracarboxylic diimide
• CAS No.: 345293-86-9
• Molecular Formula: C₃₅H₂₉N₃O₈
• Molecular Weight: 619.631
• Mol file: 345293-86-9.mol

Synonyms:

Chemical Property of N-[(p-carboxyphenyl)methyl]-N'-[(p-(N-t-BOC-aminomethyl)phenyl)methyl]-1,4,5,8-naphthalenetetracarboxylic diimide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-[(p-carboxyphenyl)methyl]-N'-[(p-(N-t-BOC-aminomethyl)phenyl)methyl]-1,4,5,8-naphthalenetetracarboxylic diimide

There total 2 articles about N-[(p-carboxyphenyl)methyl]-N'-[(p-(N-t-BOC-aminomethyl)phenyl)methyl]-1,4,5,8-naphthalenetetracarboxylic diimide 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: 26.0%

p-aminomethylbenzoic acid (56-91-7) + 1,4,5,8-naphthalenetetracarboxylic dianhydride (81-30-1) + tert-butyl 4-(aminomethyl)benzylcarbamate (108468-00-4) → N-[(p-carboxyphenyl)methyl]-N'-[(p-(N-t-BOC-aminomethyl)phenyl)methyl]-1,4,5,8-naphthalenetetracarboxylic diimide (345293-86-9)

Guidance literature:

p-aminomethylbenzoic acid; 1,4,5,8-naphthalenetetracarboxylic dianhydride; In N,N-dimethyl acetamide; at 100 ℃; for 6h;

tert-butyl 4-(aminomethyl)benzylcarbamate; In N,N-dimethyl acetamide; at 100 ℃; for 12h; Further stages.;

DOI:10.1021/jo991054y

Reference yield:

p-xylylidenediamine (539-48-0) → N-[(p-carboxyphenyl)methyl]-N'-[(p-(N-t-BOC-aminomethyl)phenyl)methyl]-1,4,5,8-naphthalenetetracarboxylic diimide (345293-86-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 30 percent / CHCl₃ / 20 h

2.1: N,N-dimethyl-acetamide / 6 h / 100 °C

2.2: 26 percent / N,N-dimethyl-acetamide / 12 h / 100 °C

In chloroform; N,N-dimethyl acetamide;

DOI:10.1021/jo991054y

Reference yield:

N-[(p-carboxyphenyl)methyl]-N'-[(p-(N-t-BOC-aminomethyl)phenyl)methyl]-1,4,5,8-naphthalenetetracarboxylic diimide (345293-86-9) → 4-[7-(4-aminomethyl-benzyl)-1,3,6,8-tetraoxo-3,6,7,8-tetrahydro-1H-benzo[lmn][3,8]phenanthrolin-2-ylmethyl]-benzoic acid

Guidance literature:

With trifluoroacetic acid; In chloroform; for 0.75h;

DOI:10.1021/jo991054y

upstream raw materials:

p-aminomethylbenzoic acid

1,4,5,8-naphthalenetetracarboxylic dianhydride

tert-butyl 4-(aminomethyl)benzylcarbamate

p-xylylidenediamine

Downstream raw materials:

N-[(p-carboxyphenyl)methyl]-N'-[(p-((S)-Val(N-t-BOC)-Leu-Ala-aminomethyl)phenyl)methyl]-1,4,5,8-naphthalenetetracarboxylic diimide

Refernces