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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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.
KeywordsStreptolidine 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).
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