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Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)
 

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Solid-phase synthesis of bis-heterocyclic compounds from resin-bound orthogonally protected lysine.

An efficient method for the solid-phase synthesis of bis-heterocyclic compounds from resin-bound orthogonally protected lysine is presented. The initial reaction step involves the exhaustive reduction of resin-bound tetra-amides using borane-THF, followed by cyclization of the resulting tetra-amine with either carbonyldiimidazole, thiocarbonyldiimidazole, or oxalyldiimidazole to generate resin-bound bis-cyclic ureas, bis-cyclic thioureas, and bis-cyclic diketopiperazines, respectively. Cleavage from the solid support using hydrogen fluoride, followed by extraction and lyophilization, yields the desired bis-heterocyclic compounds in excellent yield and high purity.[1]

References

  1. Solid-phase synthesis of bis-heterocyclic compounds from resin-bound orthogonally protected lysine. Nefzi, A., Giulianotti, M.A., Houghten, R.A. Journal of combinatorial chemistry. (2001) [Pubmed]
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