N-[[(5S)-3-[3-fluoro-4-(1-oxido-4-thiomorpholinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide

Base Information

• Chemical Name: N-[[(5S)-3-[3-fluoro-4-(1-oxido-4-thiomorpholinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide
• CAS No.: 168828-60-2
• Molecular Formula: C₁₆H₂₀FN₃O₄S
• Molecular Weight: 369.417
• Mol file: 168828-60-2.mol

Synonyms:N-[[(5S)-3-[3-fluoro-4-(1-oxido-4-thiomorpholinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide

Chemical Property of N-[[(5S)-3-[3-fluoro-4-(1-oxido-4-thiomorpholinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide

Chemical Property:

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-[[(5S)-3-[3-fluoro-4-(1-oxido-4-thiomorpholinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide

There total 12 articles about N-[[(5S)-3-[3-fluoro-4-(1-oxido-4-thiomorpholinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide 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: 95.0%

sutezolid (168828-58-8) → N-[[(5S)-3-[3-fluoro-4-(1-oxido-4-thiomorpholinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide (168828-60-2)

Guidance literature:

With sodium periodate; In methanol; at 0 ℃; for 3h;

DOI:10.1021/jm950956y

Reference yield:

3,4-difluoronitrobenzene (369-34-6) → N-[[(5S)-3-[3-fluoro-4-(1-oxido-4-thiomorpholinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide (168828-60-2)

Guidance literature:

Multi-step reaction with 10 steps

1: 99 percent / N,N-diisopropylethylamine / acetonitrile / 1.) RT, 2.) reflux, 24 h

2: H₂ / W-2 Raney nickel / H₂O; tetrahydrofuran / 2 h / 2068.6 Torr

3: NaHCO₃ / H₂O; tetrahydrofuran / 0.5 h

4: 1.) n-butyllithium / 1.) THF, hexane, -78 deg C, 30 min, 2.) THF, hexane, -78 deg C, 30 min

5: 99 percent / Et₃N / CH₂Cl₂ / 2 h / Ambient temperature

6: 96 percent / NaN₃ / dimethylformamide / 5 h / 65 °C

7: tetrahydrofuran / 2 h

8: H₂O / 10 h / 40 °C

9: pyridine / CH₂Cl₂ / Ambient temperature

10: 95 percent / sodium metaperiodate / methanol / 3 h / 0 °C

With pyridine; sodium periodate; n-butyllithium; sodium azide; water; hydrogen; sodium hydrogencarbonate; triethylamine; N-ethyl-N,N-diisopropylamine; W-2 Raney nickel; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jm950956y

Reference yield:

(4-(2-fluoro-4-nitrophenyl)thiomorpholine) (168828-70-4) → N-[[(5S)-3-[3-fluoro-4-(1-oxido-4-thiomorpholinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide (168828-60-2)

Guidance literature:

Multi-step reaction with 9 steps

1: H₂ / W-2 Raney nickel / H₂O; tetrahydrofuran / 2 h / 2068.6 Torr

2: NaHCO₃ / H₂O; tetrahydrofuran / 0.5 h

3: 1.) n-butyllithium / 1.) THF, hexane, -78 deg C, 30 min, 2.) THF, hexane, -78 deg C, 30 min

4: 99 percent / Et₃N / CH₂Cl₂ / 2 h / Ambient temperature

5: 96 percent / NaN₃ / dimethylformamide / 5 h / 65 °C

6: tetrahydrofuran / 2 h

7: H₂O / 10 h / 40 °C

8: pyridine / CH₂Cl₂ / Ambient temperature

9: 95 percent / sodium metaperiodate / methanol / 3 h / 0 °C

With pyridine; sodium periodate; n-butyllithium; sodium azide; water; hydrogen; sodium hydrogencarbonate; triethylamine; W-2 Raney nickel; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/jm950956y

upstream raw materials:

sutezolid

3,4-difluoronitrobenzene

(3-fluoro-4-thiomorpholin-4-ylphenyl)amine

(4-(2-fluoro-4-nitrophenyl)thiomorpholine)

Downstream raw materials:

N-({(5S)-3-[3-Fluoro-4-(1-imino-1-oxido-1λ4,4-thiazinan-4-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl)acetamide