Processes for the preparation of linezolid intermediate

Details Processes for the preparation of linezolid intermediate Processes for the preparation of linezolid intermediate

C - Chemistry, Metallurgy

07

D

C07D 263/20 (2006.01)

Patent

CA 2602073

The present invention provides improved methods of converting R-N-(4- morpholiyl- 3-fluorophenyl)-2-oxo-5-oxazolidinyl-methyl azide (III) to the intermediate S-N-(4- morpholinyl-3-fluorophenyl)-2-oxo-5-oxazolidinyl-methyl amine (II) that involve the production of fewer by-products than previous methods. The amine (II) may then be converted into linezolid (I) of high chemical purity with respect to the inactive R- enantiomer and bis-linezolid (IV), and is in high yield, without the need for tedious, complicated purification steps, such as chromatography.

L'invention concerne des procédés améliorés de transformation de R-N-(4-morpholinyl- 3-fluorophényl)-2-oxo-5-oxazolidinyl-méthyl azide (III) en S-N-(4- morpholinyl-3-fluorophényl)-2-oxo-5-oxazolidinyl-méthyl amine (II) intermédiaire qui impliquent la production de sous-produits moins nombreux que par des procédés antérieurs. L'amine (II) peut alors être transformée en linezolid (I) d'une pureté chimique élevée par rapport aux énantiomère R et bis-linezolid inactifs (IV) et d'un haut rendement, sans que cela requiert des étapes de purification fastidieuses et complexes, par exemple la chromatographie.

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