AcetaMide, N-[[(5S)-2-oxo-3-[4-(3-oxo-4-Morpholinyl)phenyl]-5-oxazolidinyl]Methyl]-

Base Information

• Chemical Name: AcetaMide, N-[[(5S)-2-oxo-3-[4-(3-oxo-4-Morpholinyl)phenyl]-5-oxazolidinyl]Methyl]-
• CAS No.: 1429334-00-8
• Molecular Formula: C16H19N3O5
• Molecular Weight: 333.344
• Mol file: 1429334-00-8.mol

Synonyms:AcetaMide, N-[[(5S)-2-oxo-3-[4-(3-oxo-4-Morpholinyl)phenyl]-5-oxazolidinyl]Methyl]-;(S)-N-((2-oxo-3-(4-(3-oxomorpholino)phenyl)oxazolidin-5-yl)methyl)acetamide

Chemical Property of AcetaMide, N-[[(5S)-2-oxo-3-[4-(3-oxo-4-Morpholinyl)phenyl]-5-oxazolidinyl]Methyl]-

Chemical Property:

• Boiling Point: 686.4±50.0 °C(Predicted)
• PKA: 15.53±0.46(Predicted)
• PSA: 88.18000
• Density: 1.326±0.06 g/cm3(Predicted)
• LogP: 1.03200
• Storage Temp.: Refrigerator
• Solubility.: DMSO (Slightly), Methanol (Slightly)

Purity/Quality:

NLT 98% ^*data from raw suppliers

N-[[(5S)-2-Oxo-3-[4-(3-oxo-4-morpholinyl)phenyl]-5-oxazolidinyl]methyl]-acetamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: N-[[(5S)-2-Oxo-3-[4-(3-oxo-4-morpholinyl)phenyl]-5-oxazolidinyl]methyl]-acetamide is an impurity of Rivaroxaban (R538000), which is a novel antithrombotic agent. A highly potent and selective, direct FXa inhibitor.

Technology Process of AcetaMide, N-[[(5S)-2-oxo-3-[4-(3-oxo-4-Morpholinyl)phenyl]-5-oxazolidinyl]Methyl]-

There total 8 articles about AcetaMide, N-[[(5S)-2-oxo-3-[4-(3-oxo-4-Morpholinyl)phenyl]-5-oxazolidinyl]Methyl]- 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: 93.0%

[4-(3-oxo-morpholin-4-yl)phenyl]carbamic acid benzyl ester (1313613-18-1) + N-[(2S)-2-acetoxy-3-chloropropyl]acetamide (183905-31-9) → (S)-N-[{3-(4-(3-oxomorpholin-4-yl)phenyl)-2-oxo-1,3-oxazolidin-5-yl}methyl]acetamide (1429334-00-8)

Guidance literature:

With lithium tert-butoxide; In dichloromethane; N,N-dimethyl-formamide; for 10h; Reagent/catalyst; Reflux;

Reference yield:

N-[(2S)-2-acetoxy-3-chloropropyl]acetamide (183905-31-9) + 4-(4-aminophenyl)morpholin-3-one (438056-69-0) → (S)-N-[{3-(4-(3-oxomorpholin-4-yl)phenyl)-2-oxo-1,3-oxazolidin-5-yl}methyl]acetamide (1429334-00-8)

Guidance literature:

With lithium tert-butoxide; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; at 5 - 24 ℃; for 21h;

Reference yield:

4-[4-[(5S)-5-(aminomethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl]morpholine-3-one (446292-10-0,1411775-06-8) + acetyl chloride (75-36-5) → (S)-N-[{3-(4-(3-oxomorpholin-4-yl)phenyl)-2-oxo-1,3-oxazolidin-5-yl}methyl]acetamide (1429334-00-8)

Guidance literature:

With triethylamine; In tetrahydrofuran; at 20 ℃; for 2h; Inert atmosphere;

upstream raw materials:

N-[(2S)-2-acetoxy-3-chloropropyl]acetamide

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

N-[(2S)oxiranylmethyl]acetamide

N-[(2R)-2-hydroxy-3-{[4-(3-oxomorpholin-4-yl)phenyl]amino}propyl]acetamide

Downstream raw materials:

4-[4-[(5S)-5-(aminomethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl]morpholine-3-one

Refernces

• 1、 -. "the advantage cuts down Sha Ban and intermediate preparation method". Paragraph 0074; 0094; 0095; 0096; 0097; 0098; 0099-0103. . Retrieved 2017/07/31.