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ChemicalBook CAS DataBase List (R)-[3-(3-Fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl]methyl methanesulfonate
174649-09-3

(R)-[3-(3-Fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl]methyl methanesulfonate synthesis

11synthesis methods
Methanesulfonyl chloride

124-63-0

(5R)-3-(3-Fluoro-4-(4-morpholinyl)phenyl)-5-hydroxymethyl-2-oxazolidione

168828-82-8

(R)-[3-(3-Fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl]methyl methanesulfonate

174649-09-3

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).

-

Yield: 100%

Reaction Conditions:

with triethylamine in dichloromethane at 0; for 0.5 h;

Steps:

5
To a solution of 132.8 g of (R)-N-[[3-[3-fluoro-4-morpholinyl]phenyl]-2-oxo-5- oxazolidinyl] methanol and 87.1 g of triethylamine in IL of methylene dichloride at O0C under nitrogen was added 74 gm of methanesulfonyl chloride. The reaction mixture was allowed to stir at 0°C for 30 min, then allowed to warm to ambient temperature. A white solid was precipitated. 1.75 L water, 6.50 L methylene dichloride and IL ethyl acetate mixture were added followed by stirring for 30 min. The reaction mass was filtered to get a white solid. Yield: 140 g.; Percentage: 105.42% w/w

References:

USV LIMITED WO2009/63505, 2009, A2 Location in patent:Page/Page column 14

(R)-[3-(3-Fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl]methyl methanesulfonate Related Search:

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