Reactions of Mosher-Bt Reagent 1 with Chiral Amino Acids and Di- and Tripeptides

June 27, 2024

• Title:       

  Reactions of Mosher-Bt Reagent 1 with Chiral Amino Acids and Di- and Tripeptides

• Image Source:

  1-Benzotriazol-1-yl-3,3,3-trifluoro-2-methoxy-2-phenylpropan-1-ones: Mosher-Bt reagents

• Mark:

  Table 1

• Associated context:

  The reaction of (R)-1 with (R)-tryptophan, dipeptide Gly-(R)-Phe-OH, and tripeptide Gly-(S)-Phe-(S)-Phe-OH in an acetonitrile/water (2:1) mixture at rt for 12 h gave (R)-3-(1H-indol-3-yl)-2-((R)-3,3,3-trifluoro-2-methoxy-2-phenylpropionylamino)propionic acid (R, R)-2b, (R)-3-phenyl-2-[2-((R)-3,3,3-trifluoro-2-methoxy-2-phenylpro-  pionylamino)acetylamino]propionic acid (R, R)-2c, and (S)-3-phenyl-2-{(R)-3-phenyl-2-[2-((R)-3,3,3-trifluoro-2-methoxy-2-phenylpropionylamino)acetylamino]propionylamino}-propionic acid (R, S, S)-2d, respectively, in 98, 97, and 91% yield  (Table 1).