Convenient and efficient synthesis of Boc-/Z-/Fmoc-beta-amino acids employing N-protected alpha-amino acid fluorides

J Pept Res. 2000 Apr;55(4):289-94. doi: 10.1034/j.1399-3011.2000.00683.x.

Abstract

A new and efficient method for the synthesis of N(alpha)-Fmoc-/Boc-/Z-beta-amino acids using the two-step Arndt-Eistert approach is described. Fmoc-/Boc-/Z-alpha-Amino acid fluorides were used for the acylation of diazomethane synthesizing Fmoc-/Boc-/Z-alpha-aminodiazoketones as crystalline solids with good yield and purity. They were then converted to the corresponding beta-amino acids using PhCOOAg/dioxane/H2O.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acylation
  • Amino Acids / chemical synthesis*
  • Amino Acids / chemistry
  • Diazomethane / chemistry
  • Fluorenes / chemical synthesis*
  • Fluorenes / chemistry
  • Fluorine / chemistry
  • Stereoisomerism

Substances

  • Amino Acids
  • Fluorenes
  • N(alpha)-fluorenylmethyloxycarbonylamino acids
  • Fluorine
  • Diazomethane