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A Crystallographic Study of a Highly Substituted Imidazolinone, (3S,4S,5R)-3-(((S)-4-((1H-Indol-3-yl)Methyl)-5-Oxo-4,5-Dihydro-1H-Imidazol-2-yl)Amino)-4-((Tert-Butyldimethylsilyl)Oxy)-5-Hydroxypiperidin-2-One

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Abstract

The title compound 1 has been prepared from the condensation product of a silyl protected amino-oxazoline lactam (3) and Cbz-protected l-tryptophan (4) after hydrogenolysis of the carboxybenzyl protection group. The synthesis and crystal structure of 1 is described. The compound crystallized from DMSO in the monoclinic system, P21 space group with unit cell parameters a = 9.4029(25), b = 6.2828(12), c = 20.681(45), and β = 96.505(16), Z = 2 and a cell volume of V = 1213.9(2) Å3. In the crystal lattice, 1 forms an extensive hydrogen bonded framework consisting of interconnected dimeric chains.

Graphical Abstract

The synthesis and crystal structure of the title compound is described.

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Acknowledgments

This work was supported in part by the National Institutes of Health, Grant Nos. AI72012 and CA132753. Support of the NMR facility by the National Science Foundation is acknowledged (CRIF grant CHE-0741968).

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Authors and Affiliations

  1. Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, CA, 92093, USA

    Sanjay Dutta, Sergey M. Dibrov, Cody J. Higginson & Thomas Hermann

Authors
  1. Sanjay Dutta
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  2. Sergey M. Dibrov
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  3. Cody J. Higginson
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  4. Thomas Hermann
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Corresponding author

Correspondence to Thomas Hermann.

Additional information

Sanjay Dutta, Sergey M. Dibrov contributed equally to this work.

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Dutta, S., Dibrov, S.M., Higginson, C.J. et al. A Crystallographic Study of a Highly Substituted Imidazolinone, (3S,4S,5R)-3-(((S)-4-((1H-Indol-3-yl)Methyl)-5-Oxo-4,5-Dihydro-1H-Imidazol-2-yl)Amino)-4-((Tert-Butyldimethylsilyl)Oxy)-5-Hydroxypiperidin-2-One. J Chem Crystallogr 41, 1573–1578 (2011). https://doi.org/10.1007/s10870-011-0142-3

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  • DOI: https://doi.org/10.1007/s10870-011-0142-3

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