(Z)-N,N-dimethyl-{N-tert-butoxycarbonyl-N-[2-(phenyldimethylsilyl)but-2-enyl]amino}acetamide

Base Information

• Chemical Name: (Z)-N,N-dimethyl-{N-tert-butoxycarbonyl-N-[2-(phenyldimethylsilyl)but-2-enyl]amino}acetamide
• CAS No.: 320618-87-9
• Molecular Formula: C₂₁H₃₄N₂O₃Si
• Molecular Weight: 390.598
• Mol file: 320618-87-9.mol

Synonyms:(Z)-N,N-dimethyl-{N-tert-butoxycarbonyl-N-[2-(phenyldimethylsilyl)but-2-enyl]amino}acetamide

Chemical Property of (Z)-N,N-dimethyl-{N-tert-butoxycarbonyl-N-[2-(phenyldimethylsilyl)but-2-enyl]amino}acetamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (Z)-N,N-dimethyl-{N-tert-butoxycarbonyl-N-[2-(phenyldimethylsilyl)but-2-enyl]amino}acetamide

There total 3 articles about (Z)-N,N-dimethyl-{N-tert-butoxycarbonyl-N-[2-(phenyldimethylsilyl)but-2-enyl]amino}acetamide 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: 97.0%

N-[2-(dimethylamino)-2-oxoethyl]carbamic acid 1,1-dimethylethyl ester (72287-76-4) + 1-bromo-2-(dimethylphenylsilanyl)but-2(E)-ene (320618-66-4) → (Z)-N,N-dimethyl-{N-tert-butoxycarbonyl-N-[2-(phenyldimethylsilyl)but-2-enyl]amino}acetamide (320618-87-9)

Guidance literature:

N-[2-(dimethylamino)-2-oxoethyl]carbamic acid 1,1-dimethylethyl ester; With potassium hydride; In tetrahydrofuran; at 0 ℃; for 1h;

1-bromo-2-(dimethylphenylsilanyl)but-2(E)-ene; In tetrahydrofuran; at 0 - 20 ℃; for 15h; Further stages.;

DOI:10.1039/b007586h

Reference yield:

E-1-iodo-1-(dimethylphenylsilyl)propene (101150-39-4) → (Z)-N,N-dimethyl-{N-tert-butoxycarbonyl-N-[2-(phenyldimethylsilyl)but-2-enyl]amino}acetamide (320618-87-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: DIBAL / diethyl ether / 1 h / Heating

1.2: MeLi / tetrahydrofuran / 1 h / 20 °C

1.3: diethyl ether / 14 h / 20 °C

2.1: 90 percent / PPh₃; Et₃N; Br₂ / CH₂Cl₂ / -20 °C

3.1: KH / tetrahydrofuran / 1 h / 0 °C

3.2: 97 percent / tetrahydrofuran / 15 h / 0 - 20 °C

With bromine; potassium hydride; diisobutylaluminium hydride; triethylamine; triphenylphosphine; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1039/b007586h

Reference yield:

(Z)-2-(phenyldimethylsilyl)but-2-en-1-ol (320618-65-3) → (Z)-N,N-dimethyl-{N-tert-butoxycarbonyl-N-[2-(phenyldimethylsilyl)but-2-enyl]amino}acetamide (320618-87-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 90 percent / PPh₃; Et₃N; Br₂ / CH₂Cl₂ / -20 °C

2.1: KH / tetrahydrofuran / 1 h / 0 °C

2.2: 97 percent / tetrahydrofuran / 15 h / 0 - 20 °C

With bromine; potassium hydride; triethylamine; triphenylphosphine; In tetrahydrofuran; dichloromethane;

DOI:10.1039/b007586h

upstream raw materials:

N-[2-(dimethylamino)-2-oxoethyl]carbamic acid 1,1-dimethylethyl ester

1-bromo-2-(dimethylphenylsilanyl)but-2(E)-ene

E-1-iodo-1-(dimethylphenylsilyl)propene

(Z)-2-(phenyldimethylsilyl)but-2-en-1-ol