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165800-03-3

Basic Information
CAS No.: 165800-03-3
Name: Linezolid
Article Data: 98
Molecular Structure:
Molecular Structure of 165800-03-3 (Linezolid)
Formula: C16H20FN3O4
Molecular Weight: 337.351
Synonyms: Acetamide,N-[[3-[3-fluoro-4-(4-morpholinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]-, (S)-;(S)-Linezolid;Linospan;Linox;N-[[(5S)-3-[3-Fluoro-4-(4-morpholinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide;PNU 100766;U 100766;Zyvox;
EINECS: 605-416-1
Density: 1.302 g/cm3
Melting Point: 176-178 °C
Boiling Point: 585.5 °C at 760 mmHg
Flash Point: 307.9 °C
Appearance: White solid
Hazard Symbols: HarmfulXn
Risk Codes: 20/21/22
Safety: 36
PSA: 71.11000
LogP: 1.64450
Synthetic route

(2R)-1-{acetyl[3-fluoro-4-(morpholin-4-yl)-phenyl]-3-chloropropene}acetate

165800-03-3

linezolid

Conditions
ConditionsYield
With ammonium hydroxide In methanol at 20 - 25℃; for 12h;98%
1609632-44-1

N-(3-(3-fluoro-4-(morpholin-4-yl)phenyl)-2-oxooxazolidin-5(S)-ylmethyl)amine benzoate

108-24-7

acetic anhydride

165800-03-3

linezolid

Conditions
ConditionsYield
In dichloromethane at 20 - 24℃;97%
32315-10-9

bis(trichloromethyl) carbonate

N-[(2R)-3-[[3-fluoro-4-(4-morpholinyl)phenyl]amino]-2-hydroxypropyl]acetamide

165800-03-3

linezolid

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃; for 2h;95%
With triethylamine In dichloromethane at 0 - 20℃; for 2h;95%

(S)-N-[(2-oxo-5-oxazolidinyl)methyl]acetamide

1-oxo-3-fluoro-4-(4-morpholinyl)benzene

165800-03-3

linezolid

Conditions
ConditionsYield
With triethylamine; dicyclohexyl-carbodiimide In acetonitrile at 80℃; Reagent/catalyst; Solvent; Temperature;94.2%
75-36-5

acetyl chloride

168828-90-8

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

165800-03-3

linezolid

Conditions
ConditionsYield
With triethylamine In ethyl acetate at 20℃; for 2h;92.8%
With triethylamine In dichloromethane at 0 - 20℃; for 1h;85%
With triethylamine In dichloromethane at 20℃; Inert atmosphere;73 mg

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

165800-03-3

linezolid

Conditions
ConditionsYield
With water; potassium carbonate In ethyl acetate at 60 - 65℃;92%
Stage #1: [(S)-N-[[3-(3-fluoro-4-morpholinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide dihydrochloride With potassium carbonate In water; ethyl acetate at 60 - 65℃;
Stage #2: In toluene at 20 - 100℃;
92%
With sodium hydroxide In water at 0 - 2℃;
57450-20-1

acetamide monosodium

174649-09-3

(R)-methyl methanesulfonate

165800-03-3

linezolid

Conditions
ConditionsYield
With N,N-dimethyl-formamide at 50℃; Temperature; Inert atmosphere;92%
565176-83-2

N-ethoxycarbonyl-3-fluoro-4-morpholinyl aniline

183905-31-9

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

165800-03-3

linezolid

Conditions
ConditionsYield
With lithium; tert-butyl alcohol In tetrahydrofuran; N,N-dimethyl acetamide; isopropyl alcohol at 0 - 20℃; Reagent/catalyst; Solvent; Concentration;90.3%

N-(5S)-((3-(3-fluoro-4-(4-morpholinyl)phenyl)-2-oxo-5-oxazolidinyl)methyl)acetamide phthalimide

165800-03-3

linezolid

Conditions
ConditionsYield
With hydrazine hydrate In methanol at 55℃; Concentration; Temperature; Heating; Industrial scale;90.2%
168828-84-0

(R)-5-azidomethyl-3-(3-fluoro-4-(morpholin-4-yl)phenyl)oxazolidin-2-one

507-09-5

thioacetic acid

165800-03-3

linezolid

Conditions
ConditionsYield
Stage #1: (R)-5-azidomethyl-3-(3-fluoro-4-(morpholin-4-yl)phenyl)oxazolidin-2-one; tiolacetic acid at 23℃; for 7h;
Stage #2: With potassium hydroxide In water at 23℃;
90%
at 23℃; for 7h; Inert atmosphere;90%
Ambient temperature;86%
at 20℃; for 15h;85%
at 20℃; for 15h;
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Chemistry

Molecular Structure of Acetamide,N-[[(5S)-3-[3-fluoro-4-(4-morpholinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]- (CAS NO.165800-03-3):

IUPAC Name: N-[[(5R)-3-(3-Fluoro-4-morpholin-4-ylphenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide
Molecular Weight: 337.346103 [g/mol]
Molecular Formula: C16H20FN3O4
XLogP3-AA: 0.7
H-Bond Donor: 1
H-Bond Acceptor: 6 
Index of Refraction: 1.553
Molar Refractivity: 82.96 cm3
Molar Volume: 259 cm3
Surface Tension: 47.7 dyne/cm
Density: 1.302 g/cm3
Flash Point: 307.9 °C
Enthalpy of Vaporization: 87.47 kJ/mol
Boiling Point: 585.5 °C at 760 mmHg
Vapour Pressure: 1.08E-13 mmHg at 25 °C
Appearance: White Solid
Melting Point: 176-178 °C
Classification Code: Anti-Infective Agents; Antibacterial; Enzyme Inhibitors; Protein Synthesis Inhibitors 
Product Categories: Antibacterial; Aromatics Compounds; Aromatices; Chiral Reagents; Heterocycles; Intermediates & Fine Chemicals; Pharmaceuticals

Uses

 Acetamide,N-[[(5S)-3-[3-fluoro-4-(4-morpholinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]- (CAS NO.165800-03-3) is used as prototype of the oxazolidinone antimicrobials and inhibits bacterial mRNA translation.

Safety Profile

Safety Information of Acetamide,N-[[(5S)-3-[3-fluoro-4-(4-morpholinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]- (CAS NO.165800-03-3):
Hazard Codes: HarmfulXn
Risk Statements: 20/21/22 
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.
Safety Statements: 36 
S36:Wear suitable protective clothing.

Specification

  Acetamide,N-[[(5S)-3-[3-fluoro-4-(4-morpholinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]- (CAS NO.165800-03-3), its Synonyms are Linezolid ; N-(((S)-3-(3-Fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl)methyl)acetamide ; Zivoxid ; Zyvox ; Acetamide, N-((3-(3-fluoro-4-(4-morpholinyl)phenyl)-2-oxo-5-oxazolidinyl)methyl)-, (S)- .