Synthesis of Dipeptides with [CH20] Amide Bond Mimetics

互联网2014-02-08

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This chapter describes the synthetic procedures leading to ether dipeptide isosteres of the Phe-ψ[CH ₂ O]-spiro-C _x ( 9a–9e , Fig. 1 ) and Phe-ψ[CH ₂ O]-Allylglycine ( 13 , Fig. 2 ). Development of methods which lead to mimetics of amide bonds is central to the conversion of peptide leads into pharmaceutically viable molecules. Our strategy utilizes template 1 , which provides derivatives 6b–6e upon alkylation with I, Cl-alkanes (C ₃ –C ₆ ). Subsequent Finklestein conversion to iodides 7b–7e is then followed by cyclization to spirocyclic derivatives 5b–5e (Fig. 3 ).

Figure 1. Synthesis of Phe ψ[CH ₂ O]Spiro isosteres 9a–9e .

Figure 2. Synthesis of Phe ψ[CH ₂ O]Allylglycine 13

Figure 3. Synthesis of morpholinones 5b–5e .

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