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(11R)-13-Dimethyl-ammonio-11,13-dihydro-4,5-epoxy-costunolide semifumarate.

Neelakantan S, Parkin S, Crooks PA - Acta Crystallogr Sect E Struct Rep Online (2009)

Bottom Line: Subsequent crystallization of the fumarate salt from water afforded colorless ortho-rhom-bic crystals.The amine addition is highly stereospecific yielding exclusively a single diastereomer with R-configuration at the newly formed C-11 chiral carbon.In the crystal, intermolecular O-H⋯O and N-H⋯O hydrogen bonds help to establish the packing.

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ABSTRACT
Crystals of the title salt, C(17)H(28)NO(3) (+)·C(4)H(3)O(4) (-), were obtained by reacting parthenolide with dimethyl-amine followed by conversion of the amine adduct into a water-soluble fumarate salt. Subsequent crystallization of the fumarate salt from water afforded colorless ortho-rhom-bic crystals. The amine addition is highly stereospecific yielding exclusively a single diastereomer with R-configuration at the newly formed C-11 chiral carbon. In the crystal, intermolecular O-H⋯O and N-H⋯O hydrogen bonds help to establish the packing.

No MeSH data available.


Crystal packing of (I) viewed along the a axis. H atoms have been omitted for clarity.
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Fap2: Crystal packing of (I) viewed along the a axis. H atoms have been omitted for clarity.


(11R)-13-Dimethyl-ammonio-11,13-dihydro-4,5-epoxy-costunolide semifumarate.

Neelakantan S, Parkin S, Crooks PA - Acta Crystallogr Sect E Struct Rep Online (2009)

Crystal packing of (I) viewed along the a axis. H atoms have been omitted for clarity.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC2969377&req=5

Fap2: Crystal packing of (I) viewed along the a axis. H atoms have been omitted for clarity.
Bottom Line: Subsequent crystallization of the fumarate salt from water afforded colorless ortho-rhom-bic crystals.The amine addition is highly stereospecific yielding exclusively a single diastereomer with R-configuration at the newly formed C-11 chiral carbon.In the crystal, intermolecular O-H⋯O and N-H⋯O hydrogen bonds help to establish the packing.

View Article: PubMed Central - HTML - PubMed

ABSTRACT
Crystals of the title salt, C(17)H(28)NO(3) (+)·C(4)H(3)O(4) (-), were obtained by reacting parthenolide with dimethyl-amine followed by conversion of the amine adduct into a water-soluble fumarate salt. Subsequent crystallization of the fumarate salt from water afforded colorless ortho-rhom-bic crystals. The amine addition is highly stereospecific yielding exclusively a single diastereomer with R-configuration at the newly formed C-11 chiral carbon. In the crystal, intermolecular O-H⋯O and N-H⋯O hydrogen bonds help to establish the packing.

No MeSH data available.