179910-97-5Relevant academic research and scientific papers
Synthesis of Lactam-Based Peptidomimetics from β-Keto Esters and β-Keto Amides
Abell, Andrew D.,Gardiner, James
, p. 9668 - 9672 (2007/10/03)
Pyrrolidinone-based peptidomimetics, in which the peptide bond is forced to adopt either a cis or trans geometry, have been prepared from readily available amino acids. Peptidomimetics based on amino acid side chain to side chain cyclization (17), side chain to N cyclization (18), and α-H to side chain cyclization (28) have been developed. A key step in the syntheses is the treatment of a peptide-based β-keto ester or amide with an amine. The absolute configuration of compounds 28 was established using Seebach oxazolidinone chemistry.
Self-addition products from the alkylation of amino acid-derived oxazolidinones: X-ray molecular structures of (2R,4S,1′S)-3-benzoyl-4-[benzoylamino(phenyl)methyl]-4-benzyl-2-phenyl-1, 3-oxazolidin-5-one, (2A,45,1′S)- and (2R,4S,1′R)-3-benzoyl-4-[benzoylamino(phenyl)methyl]-4-isopropyl-2-phenyl- 1,3-oxazolidin-5-one
Abell, Andrew D.,Taylor, Jane M.,Oldham, Mark D.
, p. 1299 - 1304 (2007/10/03)
The alkylation of (2R,4S)-3-benzoyl-4-benzyl-2-phenyloxazolidin-5-one 7 with diphenylmethyl bromoacetate proceeded with high diastereoselectivity, and the resulting product was hydrolysed to give [(2′R,4′5)-3′-benzoyl-4′-benzyl-5′-oxo-2′- phenyloxazolidin-4′-yl]acetic acid 9. The self-addition by-product (2R,45,1′S)-3-benzoyl-4-[benzoylamino(phenyl)methyl]-4-benzyl-2-phenyl-1, 3-oxazolidin-5-one 11 was also isolated. The structures of compound of 11 and the related self-addition products (2R,4S,1′S and 1′R)-3-benzoyl-4-[benzoylamino(phenyl)methyl]-4-isopropyl-2-phenyl-1,3- oxazolidin-5-one 20 and 21 were determined by X-ray crystallography. The mechanism of formation of the self-addition products is discussed.
