Convenient and efficient synthesis of Boc-/Z-/Fmoc-beta-amino acids employing N-protected alpha-amino acid fluorides.
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.
Ananda
K
K
Department of Studies in Chemistry, Central College, Bangalore University, India.
Gopi
H N
HN
Suresh Babu
V V
VV
D000215:Acylation; D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D003978:Diazomethane / Q000737:chemistry; D005449:Fluorenes / Q000138:chemical synthesis* / Q000737:chemistry; D005461:Fluorine / Q000737:chemistry; D013237:Stereoisomerism
D000596:Amino Acids; D005449:Fluorenes; C016456:N(alpha)-fluorenylmethyloxycarbonylamino acids; D005461:Fluorine; D003978:Diazomethane