Application of in situ silylation for improved, convenient preparation of fluorenylmethoxycarbonyl (Fmoc)-protected phosphinate amino acids.
A convenient and efficient method has been developed for the preparation of 9-fluorenylmethoxycarbonyl (Fmoc)-protected 1-aminoalkylphosphinic acids. Reproducible procedures for the synthesis and purification of free alpha-amino H-phosphinates are provided. Protection of free amino phosphinates as the N-Fmoc derivative was achieved by in situ trimethylsilylation of aminoalkylphosphinic acids, which then reacted with Fmoc-Cl to provide corresponding products in excellent yields and in high purity after simple extractive isolation. Mechanistic aspects of the silylation are discussed, and the application of the procedure to another class of amino phosphorus acids is presented.
Li
Shunzi
S
Department of Chemistry, Louisiana State University, 232 Choppin Hall, Baton Rouge, Louisiana 70803, USA.
Whitehead
John K
JK
Hammer
Robert P
RP
D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry*; D005449:Fluorenes / Q000737:chemistry*; D010446:Peptide Fragments / Q000138:chemical synthesis / Q000737:chemistry*; D010721:Phosphinic Acids / Q000737:chemistry*; D012821:Silanes / Q000737:chemistry*; D013237:Stereoisomerism
C496789:9-fluorenylmethoxycarbonyl; D000596:Amino Acids; D005449:Fluorenes; D010446:Peptide Fragments; D010721:Phosphinic Acids; D012821:Silanes