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

Base Information

• Chemical Name: 2-[4-(2-acetylamino-2-methoxycarbonyl-vinyl)-2-methoxycarbonyl-phenyl]-2-fluoro-malonic acid di-tert-butyl ester
• CAS No.: 640735-69-9
• Molecular Formula: C₂₅H₃₂FNO₉
• Molecular Weight: 509.529
• Mol file: 640735-69-9.mol

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

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

There total 2 articles about 2-[4-(2-acetylamino-2-methoxycarbonyl-vinyl)-2-methoxycarbonyl-phenyl]-2-fluoro-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: 18.0%

Methyl 2-acetamidoacrylate (35356-70-8) + fluoropropanedioic acid, 4-iodo-2-(methoxycarbonyl)phenyl-, bis(1,1-dimethylethyl) ester (640735-68-8) → 2-[4-(2-acetylamino-2-methoxycarbonyl-vinyl)-2-methoxycarbonyl-phenyl]-2-fluoro-malonic acid di-tert-butyl ester (640735-69-9)

Guidance literature:

With palladium diacetate; triethylamine; tris-(o-tolyl)phosphine; In acetonitrile; for 17h; Heating;

DOI:10.1021/jm020970s

Reference yield:

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]-2-fluoro-malonic acid di-tert-butyl ester (640735-69-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: potassium hexamethyldisilazide / tetrahydrofuran / 1 h / -70 °C

1.2: 83.7 percent / N-fluorobenzenesulfonimide / tetrahydrofuran / -70 - 20 °C

2.1: 18 percent / triethylamine; Pd(OAc)2; tri-o-tolylphosphine / acetonitrile / 17 h / Heating

With palladium diacetate; potassium hexamethylsilazane; triethylamine; tris-(o-tolyl)phosphine; In tetrahydrofuran; acetonitrile; 2.1: Heck reaction;

DOI:10.1021/jm020970s

Reference yield:

2-[4-(2-acetylamino-2-methoxycarbonyl-vinyl)-2-methoxycarbonyl-phenyl]-2-fluoro-malonic acid di-tert-butyl ester (640735-69-9) → fluoropropanedioic acid, 4-[2-(acetylamino)-2-carboxyethenyl]-2-(methoxycarbonyl)phenyl-, bis(1,1-dimethylethyl) ester (640735-73-5)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; at 20 ℃; for 18h;

DOI:10.1021/jm020970s

upstream raw materials:

Methyl 2-acetamidoacrylate

fluoropropanedioic acid, 4-iodo-2-(methoxycarbonyl)phenyl-, bis(1,1-dimethylethyl) ester

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

Downstream raw materials:

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

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