New method for the synthesis of N-methyl amino acids containing peptides by reductive methylation of amino groups on the solid phase
✍ Scribed by KALJUSTE, KALLE ;UNDÉN, ANDERS
- Book ID
- 115099547
- Publisher
- Wiley (Blackwell Publishing)
- Year
- 2009
- Tongue
- English
- Weight
- 564 KB
- Volume
- 42
- Category
- Article
- ISSN
- 0367-8377
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📜 SIMILAR VOLUMES
N-Methyl amino acids and their Fmoc derivatives are synthesized in high yield and purity on solid support using the Fukuyama amine synthesis protocol.
Barton esters were prepared starting from different carboxylic acids loaded on a Wang resin. Light induced fragmentation occurred giving a radical that reacted with CBrCl 3 to give the corresponding bromides, whereas conjugate addition to electron-poor alkenes proved to be less synthetically useful.
## N-methyl amino acids, including L-abrine, and N-alkyl amino esters, were synthesized by reductive amination of O'Donnell's Schiff base amino esters with NaBH3CN and formaldehyde, or the appropriate aldehyde in CH3CN or THF in good to excellent yields, and with high purity.
## Abstract An improved method for the preparation of Merrifield resin esters is presented. This method is rapid, is free of racemization, and is not complicated by a quaternization side reaction. Chloromethylated resin beads, __t__‐butoxycarbonyl amino acid, and potassium __t__‐butoxide are heated