(E)-ethyl 4-(N-benzyl-N-tert-butoxy-carbonylamino)but-2-enoate

Base Information

• Chemical Name: (E)-ethyl 4-(N-benzyl-N-tert-butoxy-carbonylamino)but-2-enoate
• CAS No.: 210405-62-2
• Molecular Formula: C₁₈H₂₅NO₄
• Molecular Weight: 319.401
• Mol file: 210405-62-2.mol

Synonyms:(E)-ethyl 4-(N-benzyl-N-tert-butoxy-carbonylamino)but-2-enoate

Chemical Property of (E)-ethyl 4-(N-benzyl-N-tert-butoxy-carbonylamino)but-2-enoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-ethyl 4-(N-benzyl-N-tert-butoxy-carbonylamino)but-2-enoate

There total 4 articles about (E)-ethyl 4-(N-benzyl-N-tert-butoxy-carbonylamino)but-2-enoate 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: 91.0%

diethoxyphosphoryl-acetic acid ethyl ester (867-13-0) + N-(t-butyloxycarbonyl)-N-benzylaminoacetaldehyde (136159-63-2) → (E)-ethyl 4-(N-benzyl-N-tert-butoxy-carbonylamino)but-2-enoate (210405-62-2)

Guidance literature:

With sodium hydride; In diethyl ether; at 0 - 20 ℃; for 1.4h;

DOI:10.1016/S0040-4020(98)00297-X

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → (E)-ethyl 4-(N-benzyl-N-tert-butoxy-carbonylamino)but-2-enoate (210405-62-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 63 percent / aq. NaOH / 6 h / 0 - 20 °C

2: 80 percent / oxalyl chloride; dimethyl sulfoxide; triethylamine

3: 91 percent / sodium hydride / diethyl ether / 1.4 h / 0 - 20 °C

With sodium hydroxide; oxalyl dichloride; sodium hydride; dimethyl sulfoxide; triethylamine; In diethyl ether; 1: Acylation / 2: Swern oxidation / 3: Wittig-Horner reaction;

DOI:10.1016/S0040-4020(98)00297-X

Reference yield:

N-(tert-butoxycarbonyl)-N-benzylethanolamine (121496-39-7) → (E)-ethyl 4-(N-benzyl-N-tert-butoxy-carbonylamino)but-2-enoate (210405-62-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / oxalyl chloride; dimethyl sulfoxide; triethylamine

2: 91 percent / sodium hydride / diethyl ether / 1.4 h / 0 - 20 °C

With oxalyl dichloride; sodium hydride; dimethyl sulfoxide; triethylamine; In diethyl ether; 1: Swern oxidation / 2: Wittig-Horner reaction;

DOI:10.1016/S0040-4020(98)00297-X

upstream raw materials:

diethoxyphosphoryl-acetic acid ethyl ester

N-(t-butyloxycarbonyl)-N-benzylaminoacetaldehyde

di-tert-butyl dicarbonate

N-(tert-butoxycarbonyl)-N-benzylethanolamine

Downstream raw materials:

4-(N-benzyl-N-tert-butoxy-carbonylamino)but-2-enal

4-(N-benzyl-N-tert-butoxy-carbonylamino)but-2-en-1-ol