4-{4-[(S)-5-[(((4-bromophenyl)methylene)amino)methyl]-2-oxo-1,3-oxazolidin-3-yl]phenyl}-morpholin-3-one

Base Information

• Chemical Name: 4-{4-[(S)-5-[(((4-bromophenyl)methylene)amino)methyl]-2-oxo-1,3-oxazolidin-3-yl]phenyl}-morpholin-3-one
• CAS No.: 1450916-00-3
• Molecular Formula: C₂₁H₂₀BrN₃O₄
• Molecular Weight: 458.311
• Mol file: 1450916-00-3.mol

Synonyms:4-{4-[(S)-5-[(((4-bromophenyl)methylene)amino)methyl]-2-oxo-1,3-oxazolidin-3-yl]phenyl}-morpholin-3-one

Chemical Property of 4-{4-[(S)-5-[(((4-bromophenyl)methylene)amino)methyl]-2-oxo-1,3-oxazolidin-3-yl]phenyl}-morpholin-3-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-{4-[(S)-5-[(((4-bromophenyl)methylene)amino)methyl]-2-oxo-1,3-oxazolidin-3-yl]phenyl}-morpholin-3-one

There total 3 articles about 4-{4-[(S)-5-[(((4-bromophenyl)methylene)amino)methyl]-2-oxo-1,3-oxazolidin-3-yl]phenyl}-morpholin-3-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: 60.0%

[4-(3-oxo-morpholin-4-yl)phenyl]carbamic acid benzyl ester (1313613-18-1) + (S)-1-chloro-3-{[(4-bromophenyl)methylene]amino}propan-2-ol (1450915-94-2) → 4-{4-[(S)-5-[(((4-bromophenyl)methylene)amino)methyl]-2-oxo-1,3-oxazolidin-3-yl]phenyl}-morpholin-3-one (1450916-00-3)

Guidance literature:

[4-(3-oxo-morpholin-4-yl)phenyl]carbamic acid benzyl ester; With lithium tert-butoxide; In dichloromethane; at 40 ℃; for 0.166667h;

(S)-1-chloro-3-{[(4-bromophenyl)methylene]amino}propan-2-ol; In dichloromethane; at 35 - 45 ℃; for 18h;

Reference yield:

4-(4-aminophenyl)morpholin-3-one (438056-69-0) → 4-{4-[(S)-5-[(((4-bromophenyl)methylene)amino)methyl]-2-oxo-1,3-oxazolidin-3-yl]phenyl}-morpholin-3-one (1450916-00-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: triethylamine / tetrahydrofuran; water / 0.5 h / 0 - 50 °C

2.1: lithium tert-butoxide / dichloromethane / 0.17 h / 40 °C

2.2: 18 h / 35 - 45 °C

With triethylamine; lithium tert-butoxide; In tetrahydrofuran; dichloromethane; water;

Reference yield:

4-bromo-benzaldehyde (1122-91-4) → 4-{4-[(S)-5-[(((4-bromophenyl)methylene)amino)methyl]-2-oxo-1,3-oxazolidin-3-yl]phenyl}-morpholin-3-one (1450916-00-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: ammonia / tetrahydrofuran; water / 0.25 h

1.2: 21.5 h / 22 - 45 °C

2.1: lithium tert-butoxide / dichloromethane / 0.17 h / 40 °C

2.2: 18 h / 35 - 45 °C

With ammonia; lithium tert-butoxide; In tetrahydrofuran; dichloromethane; water;

upstream raw materials:

[4-(3-oxo-morpholin-4-yl)phenyl]carbamic acid benzyl ester

(S)-1-chloro-3-{[(4-bromophenyl)methylene]amino}propan-2-ol

4-(4-aminophenyl)morpholin-3-one

4-bromo-benzaldehyde

Downstream raw materials:

Rivaroxaban

4-{4-[(5S)-5-(aminomethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl}morpholin-3-one methanesulfonic acid salt

Refernces

• 1、 -. "A PROCESS FOR THE PREPARATION OF RIVAROXABAN BASED ON THE USE OF (S)-EPICHLOROHYDRIN". Page/Page column 28. . Retrieved 2013/08/28.