(E)-methyl 3-(3,5-dibromo-4-methoxyphenyl)-2-(hydroxyimino)propanoate

Base Information

• Chemical Name: (E)-methyl 3-(3,5-dibromo-4-methoxyphenyl)-2-(hydroxyimino)propanoate
• CAS No.: 1186467-83-3
• Molecular Formula: C₁₁H₁₁Br₂NO₄
• Molecular Weight: 381.021
• Mol file: 1186467-83-3.mol

Synonyms:(E)-methyl 3-(3,5-dibromo-4-methoxyphenyl)-2-(hydroxyimino)propanoate

Chemical Property of (E)-methyl 3-(3,5-dibromo-4-methoxyphenyl)-2-(hydroxyimino)propanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-methyl 3-(3,5-dibromo-4-methoxyphenyl)-2-(hydroxyimino)propanoate

There total 4 articles about (E)-methyl 3-(3,5-dibromo-4-methoxyphenyl)-2-(hydroxyimino)propanoate 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: 94.0%

(S)-methyl 2-amino-3-(3,5-dibromo-4-methoxyphenyl)propanoate → (E)-methyl 3-(3,5-dibromo-4-methoxyphenyl)-2-(hydroxyimino)propanoate (1186467-83-3)

Guidance literature:

With sodium tungstate (VI) dihydrate; dihydrogen peroxide; In ethanol; water; at 20 ℃; for 6h; Inert atmosphere;

DOI:10.1039/c1ob06722b

Reference yield:

4-(3,5-dibromo-4-methoxybenzylidene)-2-methyloxazol-5(4H)-one (346633-39-4) + methyl iodide (74-88-4) → (E)-methyl 3-(3,5-dibromo-4-methoxyphenyl)-2-(hydroxyimino)propanoate (1186467-83-3)

Guidance literature:

4-(3,5-dibromo-4-methoxybenzylidene)-2-methyloxazol-5(4H)-one; With barium hydroxide octahydrate; In 1,4-dioxane; water; at 60 ℃; for 1h; Inert atmosphere;

With hydroxylamine hydrochloride; In 1,4-dioxane; water; at 60 ℃; for 6h; Inert atmosphere;

methyl iodide; With 1,8-diazabicyclo[5.4.0]undec-7-ene; In N,N-dimethyl-formamide; at 0 ℃; for 2h; Inert atmosphere;

DOI:10.1016/j.bmcl.2016.01.083

Reference yield:

(S)-2-amino-3-(3,5-dibromo-4-methoxyphenyl)propionic acid hydrochloride → (E)-methyl 3-(3,5-dibromo-4-methoxyphenyl)-2-(hydroxyimino)propanoate (1186467-83-3)

Guidance literature:

Multi-step reaction with 2 steps

1: thionyl chloride / 2 h / 0 °C / Inert atmosphere; Reflux

2: sodium tungstate (VI) dihydrate; dihydrogen peroxide / ethanol; water / 6 h / 20 °C / Inert atmosphere

With thionyl chloride; sodium tungstate (VI) dihydrate; dihydrogen peroxide; In ethanol; water;

DOI:10.1039/c1ob06722b

upstream raw materials:

O-Methyltyrosine

4-(3,5-dibromo-4-methoxybenzylidene)-2-methyloxazol-5(4H)-one

methyl iodide

Downstream raw materials:

(E)-3-(3,5-dibromo-4-methoxyphenyl)-2-(hydroxyimino)propanoic acid

(E)-3-(3,5-dibromo-4-methoxyphenyl)-2-hydroxyimino-N-(12-(2-methylprop-2-oxy)carbamoyl-4,9-diazadodecyl)propanamide

(E)-3-(3,5-dibromo-4-methoxyphenyl)-2-hydroxyimino-N-(3-(methylamino)propyl)propanamide

Refernces

• 1、 García, José,Pereira, Raquel,de Lera, Angel R.. "Total synthesis of the natural isoprenylcysteine carboxyl methyltransferase inhibitor spermatinamine". . p. 5028 - 5030. Retrieved 2009.