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US 10,781,170 B1Granted
Process for preparing Brivaracetam
AssigneeDivi's Laboratories, Ltd.
InventorsMurali Krishna Prasad Divi, Mysore Aswatha Narayana Rao, Shaik Nowshuddin
Life of this patent
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Abstract
A process for the preparation of Brivaracetam, an anti-convulsion drug, is provided comprising Hofmann rearrangement of (S)-3-(2-(chloroamino)-2-oxoethyl) hexanoic acid, followed by cyclization resulting in (R)-4-propyl-pyrrolidin-2-one which on condensation with bromo butyric acid or ester followed by reaction with ammonia results in Brivaracetam.
Claims4
A process for the preparation of brivaracetam having the structure:
- comprising:
- a) reacting (S)-3-(2-amino-2-oxoethyl) hexanoic acid having the structure (II):
- with a chlorinating agent selected from the group consisting of trichloroisocyanuric acid, sodium dichloroisocyanurate and N-chlorosuccinimide, in a solvent selected from the group consisting of methanol, ethanol, acetonitrile, and dimethylformamide at a temperature between 20° C. and 40° C. to produce (S)-3-(2-(chloroamino)-2-oxoethyl) hexanoic acid having the structure (III):
- b) reacting (III) with sodium hydroxide in water, initially at a temperature between 15° C. and 30° C., and later at a temperature between 85° C. and 95° C. to produce (R)-4-propyl-pyrrolidin-2-one having the structure (I)
- or optionally, the compound (III) is reacted with sodium hydroxide at a temperature between 15° C. and 30° C. to obtain (R)-3-(aminomethyl) hexanoic acid having the structure (IV)
- followed by cyclizing the compound (IV) at a temperature between 85° C. and 95° C. to form (R)-4-propyl-pyrrolidin-2-one (I)
- c) converting the reaction product of step (b) or (c) into brivaracetam.
4 more elements
A compound (S)-3-(2-(chloroamino)-2-oxoethyl) hexanoic acid having the structure (III).
Dependencies are inferred from the claim text.