2-[4-(2-acetylamino-2-methoxycarbonyl-vinyl)-2-methoxycarbonyl-phenyl]-malonic acid di-tert-butyl ester

Base Information

• Chemical Name: 2-[4-(2-acetylamino-2-methoxycarbonyl-vinyl)-2-methoxycarbonyl-phenyl]-malonic acid di-tert-butyl ester
• CAS No.: 476212-91-6
• Molecular Formula: C₂₅H₃₃NO₉
• Molecular Weight: 491.538
• Mol file: 476212-91-6.mol

Synonyms:2-[4-(2-acetylamino-2-methoxycarbonyl-vinyl)-2-methoxycarbonyl-phenyl]-malonic acid di-tert-butyl ester

Chemical Property of 2-[4-(2-acetylamino-2-methoxycarbonyl-vinyl)-2-methoxycarbonyl-phenyl]-malonic acid di-tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-[4-(2-acetylamino-2-methoxycarbonyl-vinyl)-2-methoxycarbonyl-phenyl]-malonic acid di-tert-butyl ester

There total 3 articles about 2-[4-(2-acetylamino-2-methoxycarbonyl-vinyl)-2-methoxycarbonyl-phenyl]-malonic acid di-tert-butyl ester 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:

2,5-diiodobenzoic acid (14192-12-2) → 2-[4-(2-acetylamino-2-methoxycarbonyl-vinyl)-2-methoxycarbonyl-phenyl]-malonic acid di-tert-butyl ester (476212-91-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 74.9 percent / SOCl₂ / 23 h / Heating

2.1: NaH / dioxane / 0.5 h / 20 °C

2.2: CuBr / dioxane / 0.25 h / 20 °C

2.3: 70.8 percent / dioxane / 16 h / Heating

3.1: Et₃N; Pd(OAc)2; tri-o-tolylphosphine / acetonitrile / 30 h / Heating

With palladium diacetate; thionyl chloride; sodium hydride; triethylamine; tris-(o-tolyl)phosphine; In 1,4-dioxane; acetonitrile;

DOI:10.1021/jm010927p

Reference yield:

methyl 2,5-diiodobenzoate (14192-13-3) → 2-[4-(2-acetylamino-2-methoxycarbonyl-vinyl)-2-methoxycarbonyl-phenyl]-malonic acid di-tert-butyl ester (476212-91-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: NaH / dioxane / 0.5 h / 20 °C

1.2: CuBr / dioxane / 0.25 h / 20 °C

1.3: 70.8 percent / dioxane / 16 h / Heating

2.1: Et₃N; Pd(OAc)2; tri-o-tolylphosphine / acetonitrile / 30 h / Heating

With palladium diacetate; sodium hydride; triethylamine; tris-(o-tolyl)phosphine; In 1,4-dioxane; acetonitrile;

DOI:10.1021/jm010927p

Reference yield:

Methyl 2-acetamidoacrylate (35356-70-8) + 2-(4-iodo-2-methoxycarbonylphenyl)propanedioic acid, 1,3-bis(1,1-dimethylethyl)ester (439904-24-2) → 2-[4-(2-acetylamino-2-methoxycarbonyl-vinyl)-2-methoxycarbonyl-phenyl]-malonic acid di-tert-butyl ester (476212-91-6)

Guidance literature:

With palladium diacetate; triethylamine; tris-(o-tolyl)phosphine; In acetonitrile; for 30h; Heating;

DOI:10.1021/jm010927p

upstream raw materials:

Methyl 2-acetamidoacrylate

2-(4-iodo-2-methoxycarbonylphenyl)propanedioic acid, 1,3-bis(1,1-dimethylethyl)ester

2,5-diiodobenzoic acid

methyl 2,5-diiodobenzoate

Downstream raw materials:

[4-[2-(acetylamino)-2-carboxyethenyl]-2-(methoxycarbonyl)phenyl]propanedioic acid 1,3-bis(1,1-dimethylethyl) ester

2-{4-[2-Acetylamino-2-((S)-1-biphenyl-4-ylmethyl-2-oxo-azepan-3-ylcarbamoyl)-ethyl]-2-carboxy-phenyl}-malonic acid

[4-[2-(acetylamino)-3-[[(3S)-1-[[1,1'-(biphenyl)-4-yl]methyl]-2-oxohexahydro-1H-azepin-3-yl]amino]-3-oxo-1-propenyl]-2-(methoxycarbonyl)phenyl]propanedioic acid 1,3-bis(1,1-dimethylethyl) ester

2-{4-[2-acetylamino-2-(1-biphenyl-4-ylmethyl-2-oxo-azepan-3-ylcarbamoyl)-ethyl]-2-methoxycarbonyl-phenyl}-malonic acid di-tert-butyl ester