Uses
a-Me-Gly(Ethyl)-OH is used in preparation of peptide compound comprising highly sterically hindered amino acid via reaction of electron-withdrawing group-protected N-unsubstituted-α,α-disubstituted amino acid with peptide followed by N-alkylation.
Synthesis
1.4) Compound F1 (13.8 g, 95.0 mmol) and sodium hydroxide (7.6 g, 190.08 mmol) were added sequentially to a mixture of ethanol (200 mL) and water (1:1 by volume) and heated to reflux for 4 hours. Upon completion of the reaction, the pH of the reaction mixture was adjusted to 7 with 2 M hydrochloric acid solution, followed by evaporation of the solvent. The residue was dissolved in a small amount of water and purified by strongly acidic cation exchange resin 732. The final product G1 (10 g, 90% yield) was obtained as a white solid.
Purification Methods
Crystallise it from aqueous Me2CO, or better by dissolving in H2O and adding excess Me2CO. [Baker et al. J Am Chem Soc 74 4701 1952, Greenstein & Winitz The Chemistry of the Amino Acids J. Wiley, Vol 3 p 2573-2577 1961.]
References
[1] Patent: CN108440320, 2018, A. Location in patent: Paragraph 0033; 0035; 0043
