Journal of Chemical Crystallography

, Volume 41, Issue 10, pp 1573–1578 | Cite as

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

  • Sanjay Dutta
  • Sergey M. Dibrov
  • Cody J. Higginson
  • Thomas Hermann
Original Paper


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.


Streptolidine Imidazolinone Hydrogen bonding 



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).


  1. 1.
    Haupt I, Hübener R, Thrum H (1978) J Antibiot 31:1137Google Scholar
  2. 2.
    Jackson MD, Gould SJ, Zabriskie TM (2002) J Org Chem 67:2934CrossRefGoogle Scholar
  3. 3.
    Gant TG, Meyers AI (1994) Tetrahedron 50:2297CrossRefGoogle Scholar
  4. 4.
    Dutta S, Higginson CJ, Ho BT, Rynearson KD, Dibrov SM, Hermann T (2010) Org Lett 12:360CrossRefGoogle Scholar
  5. 5.
    Bruker SAINT (2005) Bruker AXS Inc. Madison, WIGoogle Scholar
  6. 6.
    Bruker AXS (2001) SADABS: v.2.01, an empirical absorption correction program. Bruker AXS, MadisonGoogle Scholar
  7. 7.
    Sheldrick GM (1997) SHELX-97, program for crystal structure refinement. University of Gottingen, GermanyGoogle Scholar
  8. 8.
    Uppsala Software Factory (1997) Typical bond lengths.

Copyright information

© Springer Science+Business Media, LLC 2011

Authors and Affiliations

  • Sanjay Dutta
    • 1
  • Sergey M. Dibrov
    • 1
  • Cody J. Higginson
    • 1
  • Thomas Hermann
    • 1
  1. 1.Department of Chemistry and BiochemistryUniversity of California, San DiegoLa JollaUSA

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