trans-1-(benzoylamino)-3-<2-(dimethoxyphosphoryl)ethyl>cyclobutane-1-N,N-pentamethylenecarboxamide

Base Information

• Chemical Name: trans-1-(benzoylamino)-3-<2-(dimethoxyphosphoryl)ethyl>cyclobutane-1-N,N-pentamethylenecarboxamide
• CAS No.: 161181-73-3
• Molecular Formula: C₂₁H₃₁N₂O₅P
• Molecular Weight: 422.461
• Mol file: 161181-73-3.mol

Synonyms:trans-1-(benzoylamino)-3-<2-(dimethoxyphosphoryl)ethyl>cyclobutane-1-N,N-pentamethylenecarboxamide

Chemical Property of trans-1-(benzoylamino)-3-<2-(dimethoxyphosphoryl)ethyl>cyclobutane-1-N,N-pentamethylenecarboxamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of trans-1-(benzoylamino)-3-<2-(dimethoxyphosphoryl)ethyl>cyclobutane-1-N,N-pentamethylenecarboxamide

There total 14 articles about trans-1-(benzoylamino)-3-<2-(dimethoxyphosphoryl)ethyl>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:

cis-1-Azido-N,N-pentamethylene-3-(phenylsulfonyl)cyclobutane-1-carboxamide (117488-02-5) → trans-1-(benzoylamino)-3-<2-(dimethoxyphosphoryl)ethyl>cyclobutane-1-N,N-pentamethylenecarboxamide (161181-73-3)

Guidance literature:

Multi-step reaction with 11 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: 1.5 g / sodium amalgam / tetrahydrofuran; methanol / 3 h / Ambient temperature

6: tetrahydrofuran; diethyl ether

7: 1.) BuLi / 1.) THF, hexane, -78 deg C, 1 h, 2.) THF, hexane, a) -78 deg C, 40 min, b.) 1 h

8: 93 percent / NaBH₄ / ethanol / 0.25 h / Ambient temperature

9: Et₃N / CH₂Cl₂ / 20 h

10: 93 percent / BuLi / tetrahydrofuran / 3 h / -78 °C

11: H₂ / Pt₂O / ethanol / 3 h

With sodium tetrahydroborate; sodium amalgam; n-butyllithium; hydrogen; triethylamine; palladium on activated charcoal; Adam’s catalyst; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; ethyl acetate;

DOI:10.1021/jm00051a005

Reference yield:

1-Azido-3-benzenesulfonyl-cyclobutanecarbonyl chloride (161181-43-7) → trans-1-(benzoylamino)-3-<2-(dimethoxyphosphoryl)ethyl>cyclobutane-1-N,N-pentamethylenecarboxamide (161181-73-3)

Guidance literature:

Multi-step reaction with 12 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: 1.5 g / sodium amalgam / tetrahydrofuran; methanol / 3 h / Ambient temperature

7: tetrahydrofuran; diethyl ether

8: 1.) BuLi / 1.) THF, hexane, -78 deg C, 1 h, 2.) THF, hexane, a) -78 deg C, 40 min, b.) 1 h

9: 93 percent / NaBH₄ / ethanol / 0.25 h / Ambient temperature

10: Et₃N / CH₂Cl₂ / 20 h

11: 93 percent / BuLi / tetrahydrofuran / 3 h / -78 °C

12: H₂ / Pt₂O / ethanol / 3 h

With sodium tetrahydroborate; sodium amalgam; n-butyllithium; hydrogen; triethylamine; palladium on activated charcoal; Adam’s catalyst; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; ethyl acetate;

DOI:10.1021/jm00051a005

Reference yield:

cis-1-Azido-3-(phenylsulfonyl)cyclobutane-1-carboxylic acid (117488-20-7) → trans-1-(benzoylamino)-3-<2-(dimethoxyphosphoryl)ethyl>cyclobutane-1-N,N-pentamethylenecarboxamide (161181-73-3)

Guidance literature:

Multi-step reaction with 13 steps

1: SOCl₂ / 1 h / 75 °C

2: CH₂Cl₂ / 1 h / Ambient temperature

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

4: 96 percent / Heating

5: Et₃N / 1 h / 0 - 20 °C

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

7: 1.5 g / sodium amalgam / tetrahydrofuran; methanol / 3 h / Ambient temperature

8: tetrahydrofuran; diethyl ether

9: 1.) BuLi / 1.) THF, hexane, -78 deg C, 1 h, 2.) THF, hexane, a) -78 deg C, 40 min, b.) 1 h

10: 93 percent / NaBH₄ / ethanol / 0.25 h / Ambient temperature

11: Et₃N / CH₂Cl₂ / 20 h

12: 93 percent / BuLi / tetrahydrofuran / 3 h / -78 °C

13: H₂ / Pt₂O / ethanol / 3 h

With sodium tetrahydroborate; sodium amalgam; n-butyllithium; thionyl chloride; hydrogen; triethylamine; palladium on activated charcoal; Adam’s catalyst; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; ethyl acetate;

DOI:10.1021/jm00051a005

upstream raw materials:

trans-1-(benzoylamino)-3-<2-(dimethoxyphosphoryl)-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