“One-Pot” Methylation of N-Nosyl-α-amino Acid Methyl Esters with Diazomethane and Their Coupling To Prepare N-Methyl Dipeptides
- 26 August 2003
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 68 (19), 7416-7421
- https://doi.org/10.1021/jo034233v
Abstract
N-Nosyl-α-amino acid methyl esters are methylated quantitatively with diazomethane. After proper deprotection of the amino function by treatment with the reagent system mercaptoacetic acid/sodium methoxide, the obtained N-methyl amino acid methyl esters are coupled with N-Fmoc amino acid chlorides to afford the corresponding dipeptides. The obtained products do not show any detectable extent of racemization by 1H NMR and HPLC.Keywords
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