All submissions of the EM system will be redirected to Online Manuscript Submission System. Authors are requested to submit articles directly to Online Manuscript Submission System of respective journal.

Abstract

Simple and efficient protocol for synthesis of N-Boc protected oxazolidines via cyclization of chiral serine

Author(s): Saurabh Khadse, Prashant Chaudhari

In present work we wish to report synthesis and characterization of (S)- tert-butyl 4-formyl-2,2-dimethyloxazolidine-3-carboxylate (5) derivatives from L-Serine as a chiral starting material.Amino terminal of L-serine was protected by (Boc)2O (ditertiary butyl dicarbonate); Cyclization of C- and Nterminal protected á-L amino acid is achieved by refluxing itwith DMP (2, 2 dimethoxy propane) and PTSA (para toluene sulfonic acid) in benzene. Structure of the productwas confirmed by FT-IR,LC-MS, 1H NMR and13C NMR. Retention of stereochemistry was confirmed by optical rotation obtained on polarimeter. After hydrolysis of methyl ester of 2, 2- dimethyloxazolidine, alcohol as side chain obtained underwent for ‘Swern OxidationÂ’ using TFAA (Trifluoro acetic anhydride), TEA and DMSO to afford aldehyde.(S)-tert-butyl 4-formyl-2,2-dimethyloxazolidine-3-carboxylate as final product, which is important synthetic precursor for synthesis of medicinally significant candidates.


Share this