New amino acids derived from L-pyroglutamic acid: Synthesis of Trans-4-benzyl-cis-5-phenyl-L-proline, L-α-(2-benzyl-3-phenylpropyl)-glycine and L-α-(3-phenylpropyl)-glycine

Add time:08/13/2019    Source:sciencedirect.com

A convenient synthesis of three new amino acids, L-α-(3-phenylpropyl)-glycine, L-α-(2-benzyl-3-phenylpropyl)-glycine and its conformationally constrained analog, trans-4-benzyl-cis-5-phenyl-L-proline is reported. All compounds were prepared in good diastereomeric or enantiomeric purity from L-pyroglutamic acid. Trans-4-benzyl-cis-5-phenyl-L-proline was prepared by benzylation of Boc-L-Pyr-OBn, ring opening with phenyllithium and subsequent cyclisation. Hydrogenolysis under mild conditions then furnished L-α-(2-benzyl-3-phenylpropyl)-glycine. In a similar way, L-α-(3-phenylpropyl)-glycine was prepared from cis-5-phenyl-L-proline by catalytic hydrogenolysis.

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