(Z)-2-tert-Butoxycarbonylamino-3-(5-methyl-thiophen-2-yl)-acrylic acid benzyl ester

Base Information

• Chemical Name: (Z)-2-tert-Butoxycarbonylamino-3-(5-methyl-thiophen-2-yl)-acrylic acid benzyl ester
• CAS No.: 125718-68-5
• Molecular Formula: C₂₀H₂₃NO₄S
• Molecular Weight: 373.473
• Mol file: 125718-68-5.mol

Synonyms:(Z)-2-tert-Butoxycarbonylamino-3-(5-methyl-thiophen-2-yl)-acrylic acid benzyl ester

Chemical Property of (Z)-2-tert-Butoxycarbonylamino-3-(5-methyl-thiophen-2-yl)-acrylic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (Z)-2-tert-Butoxycarbonylamino-3-(5-methyl-thiophen-2-yl)-acrylic acid benzyl ester

There total 2 articles about (Z)-2-tert-Butoxycarbonylamino-3-(5-methyl-thiophen-2-yl)-acrylic acid benzyl 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: 56.0%

2-iodo-5-methylthiophene (16494-36-3) + benzyl (2-t-butoxycarbonylamino)acrylate (94882-75-4) → (Z)-2-tert-Butoxycarbonylamino-3-(5-methyl-thiophen-2-yl)-acrylic acid benzyl ester (125718-68-5)

Guidance literature:

With tetrabutyl-ammonium chloride; sodium hydrogencarbonate; palladium diacetate; In N,N-dimethyl-formamide; at 85 ℃; for 17h;

Reference yield:

2-t-butoxycarbonylamino-3-hydroxypropionic acid benzyl ester (145612-59-5) → (Z)-2-tert-Butoxycarbonylamino-3-(5-methyl-thiophen-2-yl)-acrylic acid benzyl ester (125718-68-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 83 percent / NEt₃, MsCl / CH₂Cl₂ / 1.) 0-2 deg C, 15 min, 2.) room temp., 1 h

2: 56 percent / n-Bu₄NCl, NaHCO₃ / Pd(OAc)2 / dimethylformamide / 17 h / 85 °C

With tetrabutyl-ammonium chloride; sodium hydrogencarbonate; methanesulfonyl chloride; triethylamine; palladium diacetate; In dichloromethane; N,N-dimethyl-formamide;

Reference yield: 28.0%

(Z)-2-tert-Butoxycarbonylamino-3-(5-methyl-thiophen-2-yl)-acrylic acid benzyl ester (125718-68-5) → 2-tert-Butoxycarbonylamino-3-(5-methyl-thiophen-2-yl)-propionic acid benzyl ester (125718-77-6)

Guidance literature:

With hydrogen; Wilkinson's catalyst; In ethanol; at 65 ℃; for 96h; under 760 Torr;

upstream raw materials:

2-iodo-5-methylthiophene

benzyl (2-t-butoxycarbonylamino)acrylate

2-t-butoxycarbonylamino-3-hydroxypropionic acid benzyl ester

Downstream raw materials:

2-tert-Butoxycarbonylamino-3-(5-methyl-thiophen-2-yl)-propionic acid benzyl ester