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Acta Crystallogr C. 2013 Feb;69(Pt 2):179-82. doi: 10.1107/S0108270113000954. Epub 2013 Jan 16.

Telaprevir: helical chains based on three-point hydrogen-bond connections.

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  • 1Institute of Pharmacy, University of Innsbruck, Innrain 52, 6020 Innsbruck, Austria. thomas.gelbrich@uibk.ac.at


The crystal structure of the title compound [systematic name: (1S,3aR,6aS)-2-((2S)-2-{[(2S)-2-cyclohexyl-2-(pyrazine-2-carbonylamino)acetyl]amino}-3,3-dimethylbutanoyl)-N-[(3S)-1-(cyclopropylamino)-1,2-dioxohexan-3-yl]-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrole-1-carboxamide], C(36)H(53)N(7)O(6), contains two independent molecules, which possess distinct conformations and a disordered cyclopenta[c]pyrrolidine unit. In the crystal, molecules are linked into helical chains via three-point N-H···O hydrogen-bond connections in which three NH and three carbonyl groups per molecule are utilized. The chiralities of the six stereocentres per molecule inferred from this study are in agreement with the synthetic procedure.

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