Process for preparing bicalutamide
AssigneeShilpa Medicare Limited
InventorsVimal Kumar Shrawat, Karri Papa Rao, Rafiuddin, Prashant Purohit
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Abstract
The present invention provide processes for the preparation of N-[4-Cyano-3-(trifluoro methyl)phenyl]-3-[(4-fluorophenyl)sulphonyl]-2-hydroxy-2-methyl propanamide (I). The present application also provides a method of purification of N-[4-Cyano-3-(trifluoro methyl)phenyl]-3-[(4-fluorophenyl)sulphonyl]-2-hydroxy-2-methyl propanamide (I) using ethyl acetate solvent resulting in the product, substantially free from process related impurities A, B, C and D. The crystalline product of the process according to the present invention having an XRDP pattern as per FIG. 1, is useful as an active pharmaceutical and has anti-androgenic activity.
Claims9
A process of preparation of N-[4′-cyano-3′-(trifluoromethyl)phenyl]-3-[(4″-fluoro-phenyl)sulfonyl]-2-hydroxy-2-methylpropionamide (I)—
- comprising the steps of
- a. selectively oxidizing N-[4′-Cyano-3′-(trifluoromethyl)phenyl]-3-[(4″-fluoro phenyl)thio]-2-hydroxy-2-methyl propionamide of Formula (III)
- with 1% ortho tungstic acid and aqueous hydrogen peroxide in presence of an C1-C3 organic alcohol solvent;
- b. raising the temperature to about 50° C. or more;
- c. stirring until the content of compound of formula (III) achieved till less than about 1%;
- c. isolating the solid by cooling the reaction mass;
- d. adding mixture of water and water immiscible ester solvent (about 1:2);
- e. separate the organic ester solvent layer;
- f. optionally repeat the further extraction of aqueous layer with water immiscible ester solvent;
- g. optionally adding activated carbon followed by filtering the extracted organic layer;
- h. evaporating the water immiscible ester solvent;
- and
- i. isolating the pure compound of formula (I).
Dependencies are inferred from the claim text.