Deacetyl (R)-Linezolid

Base Information

• Chemical Name: Deacetyl (R)-Linezolid
• CAS No.: 912359-80-9
• Molecular Formula: C₁₄H₁₈FN₃O₃
• Molecular Weight: 295.314
• Mol file: 912359-80-9.mol

Synonyms:(S)-[3-[3-fluoro-4-(4-morpholinyl)phenyl]-2-oxo-5-oxazolidinyl]aminomethane

Chemical Property of Deacetyl (R)-Linezolid

Chemical Property:

• Melting Point: 102-104°C
• Boiling Point: 480.0±45.0 °C(Predicted)
• PKA: 8.96±0.29(Predicted)
• Density: 1.319±0.06 g/cm3(Predicted)
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Methanol (Slightly)

Purity/Quality:

99% ^*data from raw suppliers

Deacetyl(R)-Linezolid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Deacetyl (R)-Linezolid is an impurity of (R)-Linezolid (L466505).

Technology Process of Deacetyl (R)-Linezolid

There total 14 articles about Deacetyl (R)-Linezolid 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: 28.0%

(R)-5-azidomethyl-3-(3-fluoro-4-(morpholin-4-yl)phenyl)oxazolidin-2-one (168828-84-0) → (S)-[3-[3-fluoro-4-(4-morpholinyl)phenyl]-2-oxo-5-oxazolidinyl]aminomethane (912359-80-9)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; at 20 ℃;

DOI:10.1039/d1ra04691h

Reference yield:

N-[[3-[3-fluoro-4-(4-morpholinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]amine (1352030-06-8) → (S)-[3-[3-fluoro-4-(4-morpholinyl)phenyl]-2-oxo-5-oxazolidinyl]aminomethane (912359-80-9) + (S)-N-[[3-[3-fluoro-4-[4-morpholinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]amine (168828-90-8)

Guidance literature:

N-[[3-[3-fluoro-4-(4-morpholinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]amine; With Di-p-toluoyl-L-tartaric acid; In dimethyl sulfoxide; at 20 ℃; for 3h; Resolution of racemate;

With sodium carbonate; In dichloromethane; at 20 ℃; for 1h; optical yield given as %ee;

DOI:10.5012/bkcs.2012.33.4.1389

Reference yield:

(3-fluoro-4-morpholin-4-yl-phenyl)carbamic acid tert-butyl ester (952680-48-7) → (S)-[3-[3-fluoro-4-(4-morpholinyl)phenyl]-2-oxo-5-oxazolidinyl]aminomethane (912359-80-9) + (S)-N-[[3-[3-fluoro-4-[4-morpholinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]amine (168828-90-8)

Guidance literature:

Multi-step reaction with 6 steps

1.1: potassium tert-butylate / N,N-dimethyl-formamide / 0.5 h / 0 °C

1.2: 42 h / 0 °C

2.1: trifluoroacetic acid / dichloromethane / 4 h / 20 °C

3.1: triethylamine / dichloromethane / 2.5 h / 20 °C

4.1: sodium azide / N,N-dimethyl-formamide / 3.5 h / 80 °C

5.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 12 h / 20 °C / 9000.9 Torr

6.1: Di-p-toluoyl-L-tartaric acid / dimethyl sulfoxide / 3 h / 20 °C / Resolution of racemate

6.2: 1 h / 20 °C

With sodium azide; Di-p-toluoyl-L-tartaric acid; palladium 10% on activated carbon; potassium tert-butylate; hydrogen; triethylamine; trifluoroacetic acid; In dichloromethane; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.5012/bkcs.2012.33.4.1389

upstream raw materials:

N-[[3-[3-fluoro-4-(4-morpholinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]amine

(3-fluoro-4-morpholin-4-yl-phenyl)carbamic acid tert-butyl ester

C₁₈H₂₅FN₂O₄

3-fluoro-4-(morpholinyl)aniline

Downstream raw materials:

linezolid