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US 2019/0152908 A1Published application
Processes to produce brivaracetam
AssigneeESTEVE QUIMlCA S.A.
InventorsPeng WANG, Pixu LI, Qiang WEI, Yuanhua LIU
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Abstract
The present invention provides a scalable synthesis of enantiomerically pure brivaracetam, and related derivatives.
Claims9
A process for the preparation of brivaracetam XII from VII
- wherein R1 is H, saturated or unsaturated C1-20 alkyl or C1alkyl-unsubstituted or substituted aryl;
- and X is Cl, Br, I, OMs, OTs, ONs.
A process for the preparation of VII from VI
- comprising the step of
- a) converting the compound of the formula VI to the compound of formula VII in the presence of a solvent and TMSI, TMSBr, HBr, HCl or Hl;
- or
- b) ring-opening of the compound of the formula VI and hydrolysis under basic conditions in a solvent, followed by esterification and a reaction with sulfonyl chloride, wherein the sulfonyl chloride is selected from the group consisting of MsCl, TsCl, and NsCl, to obtain the compound of formula VII;
- wherein R1 is saturated or unsaturated C1-20 alkyl or C1alkyl-unsubstituted or substituted aryl;
- and X is Cl, Br, I, OMs, OTs, or ONs.
3 more elements
A process for preparation of the compound of formula XII (brivaracetam), which comprises the step of reacting the compound of formula VI with (S)-2-aminobutanamide to produce the compound of formula XII (brivaracetam).
A compound of formula VII:
- wherein R1 is H or saturated or unsaturated C1-20 alkyl or C1alkyl-unsubstituted or substituted aryl, and X is Cl, Br, I, OMs, OTs, ONs, with the proviso that if R1 is H, X is not I.
A compound of formula IX:
- wherein R1 is saturated or unsaturated C1-20 alkyl or C1alkyl-unsubstituted or substituted aryl.
A substantially pure compound VII:
- wherein R1 is H, and X is I.
Dependencies are inferred from the claim text.