Compositions and processes of preparing and using the same
AssigneePurdue Research Foundation
InventorsDavid A. Colby, Mark V. Riofski, Changho Han
Life of this patent
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Abstract
The present invention relates to compositions, for example, the DBU/Hexafluoroacetone hydrate salt, and processes of preparing and using the same for the modification of chemical compounds via the release of trifluoroacetate. The DBU/Hexafluoroacetone hydrate salt can perform trifluoromethylation reactions on chemical compounds, such as carbonyl group-containing compounds.
Claims20
A composition comprising a base and a compound of Formula (I)
- wherein
- R1 is H, halo, or C1-8 alkyl;
- R2 is H, halo, or C1-8 alkyl;
- and
- R3 is H, halo, C2-8 alkenyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, (CO)R6, (CO)OR6, (CO)SR6, (CO)NR6R7, (SO2)R6, (PO)R6R7, or C(NR6)R7, wherein R6 and R7 are independently selected from H, C1-8 alkyl, O—C1-5 alkyl, C3-6 cycloalkyl, aryl-C1-5 alkyl, and heteroaryl-C1-5 alkyl, aryl, substituted aryl, heteroaryl, and substituted heteoaryl
- or R2 and R3, together with the carbon atom to which they are attached, form a 4-7 membered cycloalkyl group or cyclo(hetero)alkyl group.
A hexafluoroacetone hydrate and DBU salt represented by the formula:
A process for the modification of a chemical compound via the release of trifluoroacetate, the process comprising the step of
- (a) reacting the chemical compound with a composition comprising a base and a compound of Formula (I)
- wherein:
- R1 is H, halo, or C1-8 alkyl;
- R2 is H, halo, or C1-8 alkyl;
- and
- R3 is H, halo, C2-8 alkenyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, (CO)R6, (CO)OR6, (CO)SR6, (CO)NR6R7, (SO2)R6, (PO)R6R7, or C(NR6)R7, wherein R6 and R7 are independently selected from H, C1-8 alkyl, O—C1-5 alkyl, C3-6 cycloalkyl, aryl-C1-5 alkyl, and heteroaryl-C1-5 alkyl, aryl, substituted aryl, heteroaryl, and substituted heteoaryl;
- or R2 and R3, together with the carbon atom to which they are attached, form a 4-7 membered cycloalkyl group or cyclo(hetero)alkyl group.
A process for preparing a composition comprising a base and a compound of formula (I)
- wherein:
- R1 is H, halo, or C1-8 alkyl;
- R2 is H, halo, or C1-8 alkyl;
- and
- R3 is H, halo, C2-8 alkenyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, (CO)R6, (CO)OR6, (CO)SR6, (CO)NR6R7, (SO2)R6, (PO)R6R7, or C(NR6)R7, wherein R6 and R7 are independently selected from H, C1-8 alkyl, O—C1-5 alkyl, C3-6 cycloalkyl, aryl-C1-5 alkyl, and heteroaryl-C1-5 alkyl, aryl, substituted aryl, heteroaryl, and substituted heteoaryl;
- or R2 and R3, together with the carbon atom to which they are attached, form a 4-7 membered cycloalkyl group or cyclo(hetero)alkyl group,
- the process comprising the step of
- (a) reacting the base with the compound of Formula (I) in a solvent to form the composition.
Dependencies are inferred from the claim text.