(2R,3R)-3-(4-chlorophenyl)-3-hydroxy-1-[(S)-5-isopropyl-3-phenyl-2-thioxoimidazolidin-1-yl]-2-methylpropan-1-one

Base Information

• Chemical Name: (2R,3R)-3-(4-chlorophenyl)-3-hydroxy-1-[(S)-5-isopropyl-3-phenyl-2-thioxoimidazolidin-1-yl]-2-methylpropan-1-one
• CAS No.: 1350820-15-3
• Molecular Formula: C₂₂H₂₅ClN₂O₂S
• Molecular Weight: 416.972
• Mol file: 1350820-15-3.mol

Synonyms:(2R,3R)-3-(4-chlorophenyl)-3-hydroxy-1-[(S)-5-isopropyl-3-phenyl-2-thioxoimidazolidin-1-yl]-2-methylpropan-1-one

Chemical Property of (2R,3R)-3-(4-chlorophenyl)-3-hydroxy-1-[(S)-5-isopropyl-3-phenyl-2-thioxoimidazolidin-1-yl]-2-methylpropan-1-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R)-3-(4-chlorophenyl)-3-hydroxy-1-[(S)-5-isopropyl-3-phenyl-2-thioxoimidazolidin-1-yl]-2-methylpropan-1-one

There total 5 articles about (2R,3R)-3-(4-chlorophenyl)-3-hydroxy-1-[(S)-5-isopropyl-3-phenyl-2-thioxoimidazolidin-1-yl]-2-methylpropan-1-one 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: 68.0%

(S)-N-propionyl-4-isopropyl-1-phenylimidazolidin-2-thione (1350820-10-8) + 4-chlorobenzaldehyde (104-88-1) → (2R,3R)-3-(4-chlorophenyl)-3-hydroxy-1-[(S)-5-isopropyl-3-phenyl-2-thioxoimidazolidin-1-yl]-2-methylpropan-1-one (1350820-15-3)

Guidance literature:

(S)-N-propionyl-4-isopropyl-1-phenylimidazolidin-2-thione; With titanium tetrachloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at -78 ℃; for 1.16667h; Inert atmosphere;

4-chlorobenzaldehyde; In dichloromethane; at -78 ℃; for 0.5h; optical yield given as %de; stereoselective reaction; Inert atmosphere;

DOI:10.1055/s-0030-1260187

Reference yield:

(S)-4-isopropyl-1-phenylimidazolidin-2-thione (433285-46-2) → (2R,3R)-3-(4-chlorophenyl)-3-hydroxy-1-[(S)-5-isopropyl-3-phenyl-2-thioxoimidazolidin-1-yl]-2-methylpropan-1-one (1350820-15-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium hydride / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere

1.2: 1 h / 0 °C / Inert atmosphere

2.1: titanium tetrachloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 1.17 h / -78 °C / Inert atmosphere

2.2: 0.5 h / -78 °C / Inert atmosphere

With titanium tetrachloride; sodium hydride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; 2.1: Aldol condensation / 2.2: Aldol condensation;

DOI:10.1055/s-0030-1260187

Reference yield:

L-valine (72-18-4,25609-85-2,7004-03-7,921-10-8) → (2R,3R)-3-(4-chlorophenyl)-3-hydroxy-1-[(S)-5-isopropyl-3-phenyl-2-thioxoimidazolidin-1-yl]-2-methylpropan-1-one (1350820-15-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: triethylamine / 1,4-dioxane; water / 1 h / 0 °C

1.2: 12 h / 20 °C / pH 2

2.1: lithium aluminium tetrahydride / diethyl ether / 12 h / Inert atmosphere; Reflux

3.1: sodium hydride / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere

3.2: 1 h / 0 °C / Inert atmosphere

4.1: titanium tetrachloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 1.17 h / -78 °C / Inert atmosphere

4.2: 0.5 h / -78 °C / Inert atmosphere

With lithium aluminium tetrahydride; titanium tetrachloride; sodium hydride; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; 1,4-dioxane; diethyl ether; dichloromethane; water; 4.1: Aldol condensation / 4.2: Aldol condensation;

DOI:10.1055/s-0030-1260187

upstream raw materials:

(S)-4-isopropyl-1-phenylimidazolidin-2-thione

(S)-N-propionyl-4-isopropyl-1-phenylimidazolidin-2-thione

4-chlorobenzaldehyde

L-valine