cis-3-<<(1,1-dimethylethoxy)carbonyl>amino>-2-oxo-4-(2-phenylethenyl)-1-azetidine

Base Information

• Chemical Name: cis-3-<<(1,1-dimethylethoxy)carbonyl>amino>-2-oxo-4-(2-phenylethenyl)-1-azetidine
• CAS No.: 81741-02-8
• Molecular Formula: C₁₆H₂₀N₂O₃
• Molecular Weight: 288.346
• Mol file: 81741-02-8.mol

Synonyms:cis-3-<<(1,1-dimethylethoxy)carbonyl>amino>-2-oxo-4-(2-phenylethenyl)-1-azetidine

Chemical Property of cis-3-<<(1,1-dimethylethoxy)carbonyl>amino>-2-oxo-4-(2-phenylethenyl)-1-azetidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of cis-3-<<(1,1-dimethylethoxy)carbonyl>amino>-2-oxo-4-(2-phenylethenyl)-1-azetidine

There total 4 articles about cis-3-<<(1,1-dimethylethoxy)carbonyl>amino>-2-oxo-4-(2-phenylethenyl)-1-azetidine 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: 48.0%

[(3S,4R)-1-(4-Methoxy-phenyl)-2-oxo-4-((E)-styryl)-azetidin-3-yl]-carbamic acid tert-butyl ester (81741-01-7) → cis-3-<<(1,1-dimethylethoxy)carbonyl>amino>-2-oxo-4-(2-phenylethenyl)-1-azetidine (81741-02-8)

Guidance literature:

With ammonium cerium(IV) nitrate; In acetonitrile; at -5 - 0 ℃; for 0.416667h;

DOI:10.1021/jo00135a016

Reference yield:

(E)-3-phenylpropenal (14371-10-9) → cis-3-<<(1,1-dimethylethoxy)carbonyl>amino>-2-oxo-4-(2-phenylethenyl)-1-azetidine (81741-02-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 88 percent / MgSO₄ / CH₂Cl₂ / 2 h / 0 °C

2: 60 percent / 1.) Et₃N, 2.) trifluoroacetic anhydride / CH₂Cl₂ / 1.) 0 deg C, 2.) 0 deg C, 1 h, 3.) room temperature, 12 h

3: Zn / acetic acid

4: 48 percent / ceric ammonium nitrate (CAN) / acetonitrile / 0.42 h / -5 - 0 °C

With ammonium cerium(IV) nitrate; magnesium sulfate; triethylamine; trifluoroacetic anhydride; zinc; In dichloromethane; acetic acid; acetonitrile;

DOI:10.1021/jo00135a016

Reference yield:

N-cinnamylidene-p-anisidine (80542-40-1) → cis-3-<<(1,1-dimethylethoxy)carbonyl>amino>-2-oxo-4-(2-phenylethenyl)-1-azetidine (81741-02-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 60 percent / 1.) Et₃N, 2.) trifluoroacetic anhydride / CH₂Cl₂ / 1.) 0 deg C, 2.) 0 deg C, 1 h, 3.) room temperature, 12 h

2: Zn / acetic acid

3: 48 percent / ceric ammonium nitrate (CAN) / acetonitrile / 0.42 h / -5 - 0 °C

With ammonium cerium(IV) nitrate; triethylamine; trifluoroacetic anhydride; zinc; In dichloromethane; acetic acid; acetonitrile;

DOI:10.1021/jo00135a016

upstream raw materials:

[(3S,4R)-1-(4-Methoxy-phenyl)-2-oxo-4-((E)-styryl)-azetidin-3-yl]-carbamic acid tert-butyl ester

(E)-3-phenylpropenal

N-cinnamylidene-p-anisidine

cis-3-azido-1-(4-methoxyphenyl)-2-oxo-4-(2-phenylethenyl)azetidine