| Identification | Back Directory | [Name]
(R)-[3-(3-Fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl]methyl methanesulfonate | [CAS]
174649-09-3 | [Synonyms]
Linezolid USP RC D
Linezolid Impurity 32
Mesylate imp USP RC-D
Linezolid Impurity1318
Linezolid related Compound
Linezolid Related Compound 1
Linezolid USP Related Compound D
Linezolid Related Compound D (Linezolid Mesylate Impurity)
(R)-[3-(3-Fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl]me...
(R)-N-(3-(3-Fluoro-(4-morpholinyl)phenyl)-2-oxo-5-oxazolidinyl)methanol mesylate
(R)-[3-(3-Fluoro-4-Morpholinophenyl)-2-oxo-5-oxazolidinyl]Methyl Methanesulfonat
(R)-(3-(3-flouro-4-Morpholinophenyl)-2-oxo-5-oxazolidinyl)Methyl Methanesulfonate
(R)-(3-(3-Fluoro-4-morpholinophenyl)-2-oxooxazolidin-5-yl)methyl methanesulfonate
(R)-[3-(3-Fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl]methyl methanesulfonate
(R)-3-(3-Fluoro-4-morpholin-4-ylphenyl)-2-oxo-5-oxazolidinyl)methyl methansulfonate
(5R)-3-[3-Fluoro-4-(4-Morpholinyl)phenyl]-5-[[(Methylsulfonyl)oxy]Methyl]-2-oxazolidinone
2-Oxazolidinone, 3-[3-fluoro-4-(4-Morpholinyl)phenyl]-5-[[(Methylsulfonyl)oxy]Methyl]-, (5R)-
TIANFU-CHEM --(R)-[3-(3-Fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl]methyl methanesulfonate | [EINECS(EC#)]
1592732-453-0 | [Molecular Formula]
C15H19FN2O6S | [MDL Number]
MFCD18070719 | [MOL File]
174649-09-3.mol | [Molecular Weight]
374.385 |
| Chemical Properties | Back Directory | [Melting point ]
183-185℃ | [Boiling point ]
592.7±50.0 °C(Predicted) | [density ]
1.418 | [storage temp. ]
2-8°C | [solubility ]
Chloroform (Slightly, Heated), DMSO (Slightly), Methanol (Slightly, Heated) | [form ]
Solid | [pka]
5.71±0.40(Predicted) | [color ]
White to Off-White |
| Hazard Information | Back Directory | [Uses]
(5R)-3-[3-Fluoro-4-(4-morpholinyl)phenyl]-5-[[(methylsulfonyl)oxy]methyl]-2-oxazolidinone (Linezolid USP Related Compound D) is an intermediate in the synthesis of Linezolid Dimer (L466520), an impurity of the antibacterial agent Linezolid (L466500). | [Synthesis]
To a 1L solution of dichloromethane containing 132.8 g of (R)-3-[3-fluoro-4-(4-morpholinyl)phenyl]-5-hydroxymethyl-2-oxazolidinone and 87.1 g of triethylamine was slowly added 74 g of methanesulfonyl chloride at 0°C under nitrogen protection. The reaction mixture was stirred at 0 °C for 30 min and then gradually warmed up to room temperature. A white solid precipitated during the reaction. Subsequently, a solvent mixture consisting of 1.75 L of water, 6.50 L of dichloromethane and 1 L of ethyl acetate was added to the reaction system and stirring was continued for 30 minutes. Upon completion of the reaction, the white solid product was collected by filtration. A final product of 140 g was obtained with a yield of 105.42% (w/w). | [References]
[1] Patent: WO2009/63505, 2009, A2. Location in patent: Page/Page column 14
[2] Patent: EP2163547, 2010, A1. Location in patent: Page/Page column 8
[3] Patent: WO2011/77310, 2011, A1. Location in patent: Page/Page column 12; 13
[4] Synthetic Communications, 2010, vol. 40, # 6, p. 789 - 798
[5] Patent: WO2010/84514, 2010, A2. Location in patent: Page/Page column 15 |
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