3-(3,5-dibromo-4-methoxy-2-methoxymethoxy-phenyl)-2-hydroxyimino-N-[2-(3H-imidazol-4-yl)-ethyl]-propionamide

Base Information

• Chemical Name: 3-(3,5-dibromo-4-methoxy-2-methoxymethoxy-phenyl)-2-hydroxyimino-N-[2-(3H-imidazol-4-yl)-ethyl]-propionamide
• CAS No.: 343256-39-3
• Molecular Formula: C₁₇H₂₀Br₂N₄O₅
• Molecular Weight: 520.178
• Mol file: 343256-39-3.mol

Synonyms:3-(3,5-dibromo-4-methoxy-2-methoxymethoxy-phenyl)-2-hydroxyimino-N-[2-(3H-imidazol-4-yl)-ethyl]-propionamide

Chemical Property of 3-(3,5-dibromo-4-methoxy-2-methoxymethoxy-phenyl)-2-hydroxyimino-N-[2-(3H-imidazol-4-yl)-ethyl]-propionamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-(3,5-dibromo-4-methoxy-2-methoxymethoxy-phenyl)-2-hydroxyimino-N-[2-(3H-imidazol-4-yl)-ethyl]-propionamide

There total 5 articles about 3-(3,5-dibromo-4-methoxy-2-methoxymethoxy-phenyl)-2-hydroxyimino-N-[2-(3H-imidazol-4-yl)-ethyl]-propionamide 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: 96.0%

methyl 3-{3,5-dibromo-4-methoxy-2-(O-methoxymethylenoxy)phenyl}2(E)-(hydroxyimino)propanoate (343256-46-2) + histamine (51-45-6) → 3-(3,5-dibromo-4-methoxy-2-methoxymethoxy-phenyl)-2-hydroxyimino-N-[2-(3H-imidazol-4-yl)-ethyl]-propionamide (343256-39-3)

Guidance literature:

In methanol; at 60 ℃; for 72h;

DOI:10.1021/jo010015v

Reference yield:

2-Hydroxy-4-methoxybenzaldehyde (673-22-3) → 3-(3,5-dibromo-4-methoxy-2-methoxymethoxy-phenyl)-2-hydroxyimino-N-[2-(3H-imidazol-4-yl)-ethyl]-propionamide (343256-39-3)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 97 percent / NBS / dimethylformamide / 0.25 h / 0 °C

2.1: 99 percent / iPr₂NEt / tetrahydrofuran / 0 - 20 °C

3.1: 92 percent / iPr₂NH; n-BuLi / tetrahydrofuran / -78 °C

4.1: Et₃N*HF / methanol

4.2: 90 percent / NH₂OH*HCl / methanol

5.1: 96 percent / methanol / 72 h / 60 °C

With N-Bromosuccinimide; n-butyllithium; triethylamine hydrofluoride; diisopropylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; 3.1: Wadsworth-Emmons olefination;

DOI:10.1021/jo010015v

Reference yield:

3,5-dibromo-2-hydroxy-4-methoxy benzaldehyde (117238-61-6) → 3-(3,5-dibromo-4-methoxy-2-methoxymethoxy-phenyl)-2-hydroxyimino-N-[2-(3H-imidazol-4-yl)-ethyl]-propionamide (343256-39-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 99 percent / iPr₂NEt / tetrahydrofuran / 0 - 20 °C

2.1: 92 percent / iPr₂NH; n-BuLi / tetrahydrofuran / -78 °C

3.1: Et₃N*HF / methanol

3.2: 90 percent / NH₂OH*HCl / methanol

4.1: 96 percent / methanol / 72 h / 60 °C

With n-butyllithium; triethylamine hydrofluoride; diisopropylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; 2.1: Wadsworth-Emmons olefination;

DOI:10.1021/jo010015v

upstream raw materials:

methyl 3-{3,5-dibromo-4-methoxy-2-(O-methoxymethylenoxy)phenyl}2(E)-(hydroxyimino)propanoate

histamine

2-Hydroxy-4-methoxybenzaldehyde

3,5-dibromo-2-hydroxy-4-methoxy benzaldehyde