1010422-86-2Relevant articles and documents
Practical synthesis of a peptide deformylase (PDF) inhibitor
Liu, Yugang,Prashad, Mahavir,Ciszewski, Lech,Vargas, Kevin,Repic, Oljan,Blacklock, Thomas J.
, p. 183 - 191 (2008)
A practical chromatography-free synthesis of an N-formylated hydroxylamine peptide deformylase inhibitor LCD320 is described. A diastereoselective Michael reaction of (4S)-3-[2-(cyclobutylmethyl)-l-oxo-2-propenyl]-4-(phenylmethyl)-2- oxazolidinone with 0-benzyl hydroxylamine was used to establish the key stereogenic center. We found that traces of residual Li+ from a previous step had a great impact on the diastereoselectivity of this reaction. A very efficient amidalion coupling reaction of proline derivative (2S,4R)-4-fluoro-1,2-m-pyrrolidinedicarboxylic acid 1,1-dimethylethyl ester with weakly nucleophilic 3-pyridazinamine using methanesulfonyl chloride in the presence of l-methylimidazole in DMF was also developed that proceeded without racemization.
