|
|
| | (R)-[3-(3-Fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl]methyl methanesulfonate Basic information |
| Product Name: | (R)-[3-(3-Fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl]methyl methanesulfonate | | Synonyms: | (R)-[3-(3-Fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl]methyl methanesulfonate;(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;(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)-;Linezolid related Compound;Linezolid USP RC D | | CAS: | 174649-09-3 | | MF: | C15H19FN2O6S | | MW: | 374.38 | | EINECS: | 1592732-453-0 | | Product Categories: | | | Mol File: | 174649-09-3.mol | ![(R)-[3-(3-Fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl]methyl methanesulfonate Structure](CAS2/GIF/174649-09-3.gif) |
| | (R)-[3-(3-Fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl]methyl methanesulfonate Chemical Properties |
| 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 | | Major Application | pharmaceutical | | InChI | 1S/C15H19FN2O6S/c1-25(20,21)23-10-12-9-18(15(19)24-12)11-2-3-14(13(16)8-11)17-4-6-22-7-5-17/h2-3,8,12H,4-7,9-10H2,1H3/t12-/m1/s1 | | InChIKey | UCVIKCGVGWBTTI-GFCCVEGCSA-N | | SMILES | Fc1c(ccc(c1)N3C[C@@H](OC3=O)CO[S](=O)(=O)C)N2CCOCC2 |
| WGK Germany | WGK 3 | | HS Code | 2934990002 | | Storage Class | 11 - Combustible Solids |
| | (R)-[3-(3-Fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl]methyl methanesulfonate Usage And Synthesis |
| 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 |
| | (R)-[3-(3-Fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl]methyl methanesulfonate Preparation Products And Raw materials |
|