cis-1-(benzoylamino)-3-<2-(methoxycarbonyl)etyl>cyclobutane-1-N,N-pentamethylenecarboxamide

Base Information

• Chemical Name: cis-1-(benzoylamino)-3-<2-(methoxycarbonyl)etyl>cyclobutane-1-N,N-pentamethylenecarboxamide
• CAS No.: 161181-56-2
• Molecular Formula: C₂₁H₂₈N₂O₄
• Molecular Weight: 372.464
• Mol file: 161181-56-2.mol

Synonyms:cis-1-(benzoylamino)-3-<2-(methoxycarbonyl)etyl>cyclobutane-1-N,N-pentamethylenecarboxamide

Chemical Property of cis-1-(benzoylamino)-3-<2-(methoxycarbonyl)etyl>cyclobutane-1-N,N-pentamethylenecarboxamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of cis-1-(benzoylamino)-3-<2-(methoxycarbonyl)etyl>cyclobutane-1-N,N-pentamethylenecarboxamide

There total 13 articles about cis-1-(benzoylamino)-3-<2-(methoxycarbonyl)etyl>cyclobutane-1-N,N-pentamethylenecarboxamide 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: 100.0%

cis-1-(benzoylamino)-3-<2-(methoxycarbonyl)ethenyl>cyclobutane-1-N,N-pentamethylenecarboxamide (161181-55-1) → cis-1-(benzoylamino)-3-<2-(methoxycarbonyl)etyl>cyclobutane-1-N,N-pentamethylenecarboxamide (161181-56-2)

Guidance literature:

With hydrogen; platinum(IV) oxide; In ethanol; for 2h;

DOI:10.1021/jm00051a005

Reference yield:

cis-1-Azido-N,N-pentamethylene-3-(phenylsulfonyl)cyclobutane-1-carboxamide (117488-02-5) → cis-1-(benzoylamino)-3-<2-(methoxycarbonyl)etyl>cyclobutane-1-N,N-pentamethylenecarboxamide (161181-56-2)

Guidance literature:

Multi-step reaction with 10 steps

1: H₂ / Pd/C / ethyl acetate / 20 h / 760 Torr

2: 96 percent / Heating

3: Et₃N / 1 h / 0 - 20 °C

4: 1.) BuLi / 1.) THF, -40 deg C - -50 deg C, 1 h, 2.) THF, -50 deg C, - RT

5: 0.4 g / sodium amalgam / tetrahydrofuran; methanol / 3 h / Ambient temperature

6: tetrahydrofuran; diethyl ether

7: 70 percent / NaBH₄ / dioxane; H₂O / 20 h / Ambient temperature

8: 63 percent / DMSO, TFAA / CH₂Cl₂ / 3 h

9: 77 percent / benzene / 20 h / 80 °C

10: 100 percent / H₂ / PtO₂ / ethanol / 2 h

With sodium tetrahydroborate; sodium amalgam; n-butyllithium; hydrogen; dimethyl sulfoxide; triethylamine; trifluoroacetic anhydride; platinum(IV) oxide; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; ethanol; dichloromethane; water; ethyl acetate; benzene;

DOI:10.1021/jm00051a005

Reference yield:

1-Azido-3-benzenesulfonyl-cyclobutanecarbonyl chloride (161181-43-7) → cis-1-(benzoylamino)-3-<2-(methoxycarbonyl)etyl>cyclobutane-1-N,N-pentamethylenecarboxamide (161181-56-2)

Guidance literature:

Multi-step reaction with 11 steps

1: CH₂Cl₂ / 1 h / Ambient temperature

2: H₂ / Pd/C / ethyl acetate / 20 h / 760 Torr

3: 96 percent / Heating

4: Et₃N / 1 h / 0 - 20 °C

5: 1.) BuLi / 1.) THF, -40 deg C - -50 deg C, 1 h, 2.) THF, -50 deg C, - RT

6: 0.4 g / sodium amalgam / tetrahydrofuran; methanol / 3 h / Ambient temperature

7: tetrahydrofuran; diethyl ether

8: 70 percent / NaBH₄ / dioxane; H₂O / 20 h / Ambient temperature

9: 63 percent / DMSO, TFAA / CH₂Cl₂ / 3 h

10: 77 percent / benzene / 20 h / 80 °C

11: 100 percent / H₂ / PtO₂ / ethanol / 2 h

With sodium tetrahydroborate; sodium amalgam; n-butyllithium; hydrogen; dimethyl sulfoxide; triethylamine; trifluoroacetic anhydride; platinum(IV) oxide; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; ethanol; dichloromethane; water; ethyl acetate; benzene;

DOI:10.1021/jm00051a005

upstream raw materials:

cis-1-(benzoylamino)-3-<2-(methoxycarbonyl)ethenyl>cyclobutane-1-N,N-pentamethylenecarboxamide

benzoyl chloride

cis-1-Azido-N,N-pentamethylene-3-(phenylsulfonyl)cyclobutane-1-carboxamide

1-Azido-3-benzenesulfonyl-cyclobutanecarbonyl chloride

Refernces