(3R,4S)-1-(tert-butoxycarbonyl)-4-cyclohexyl-3-(1-ethoxyethoxy)-2-azetidinone

Base Information

• Chemical Name: (3R,4S)-1-(tert-butoxycarbonyl)-4-cyclohexyl-3-(1-ethoxyethoxy)-2-azetidinone
• CAS No.: 201856-60-2
• Molecular Formula: C₁₈H₃₁NO₅
• Molecular Weight: 341.448
• Mol file: 201856-60-2.mol

Synonyms:(3R,4S)-1-(tert-butoxycarbonyl)-4-cyclohexyl-3-(1-ethoxyethoxy)-2-azetidinone

Chemical Property of (3R,4S)-1-(tert-butoxycarbonyl)-4-cyclohexyl-3-(1-ethoxyethoxy)-2-azetidinone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4S)-1-(tert-butoxycarbonyl)-4-cyclohexyl-3-(1-ethoxyethoxy)-2-azetidinone

There total 4 articles about (3R,4S)-1-(tert-butoxycarbonyl)-4-cyclohexyl-3-(1-ethoxyethoxy)-2-azetidinone 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%

di-tert-butyl dicarbonate (24424-99-5) + 3-(1-ethoxyethoxy)-4-cyclohexyl-2-azetidinone (201856-52-2) → (3R,4S)-1-(tert-butoxycarbonyl)-4-cyclohexyl-3-(1-ethoxyethoxy)-2-azetidinone (201856-60-2)

Guidance literature:

With dmap; triethylamine; In dichloromethane; for 4h; Ambient temperature;

DOI:10.1021/jm00042a013

Reference yield:

(3R,4S)-3-hydroxy-4-phenylazetidin-2-one (132127-34-5) → (3R,4S)-1-(tert-butoxycarbonyl)-4-cyclohexyl-3-(1-ethoxyethoxy)-2-azetidinone (201856-60-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 85 percent / H₂ / 5percent Rh/C / methanol / 120 h / 90 °C / 41371.8 Torr

2: 100 percent / p-toluenesulfonic acid / tetrahydrofuran / 2 h / 0 °C

3: 91 percent / DMAP, Et₃N / CH₂Cl₂ / 4 h / Ambient temperature

With dmap; hydrogen; toluene-4-sulfonic acid; triethylamine; Rh on carbon; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/jm00042a013

Reference yield:

(3R,4S)-4-cyclohexyl-3-hydroxy-2-azetidinone (156742-11-9) → (3R,4S)-1-(tert-butoxycarbonyl)-4-cyclohexyl-3-(1-ethoxyethoxy)-2-azetidinone (201856-60-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / p-toluenesulfonic acid / tetrahydrofuran / 2 h / 0 °C

2: 91 percent / DMAP, Et₃N / CH₂Cl₂ / 4 h / Ambient temperature

With dmap; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jm00042a013

upstream raw materials:

di-tert-butyl dicarbonate

3-(1-ethoxyethoxy)-4-cyclohexyl-2-azetidinone

(3R,4S)-3-hydroxy-4-phenylazetidin-2-one

(3R,4S)-4-cyclohexyl-3-hydroxy-2-azetidinone