Synthesis of N^α-Protected Amino Acid–Derived Selenocarbamates Employing Isocyanates as Key Intermediates

Abstract

A simple protocol for the synthesis of N ^α -urethane-protected N-alkyl-Se-alkyl selenocarbamate derivatives of amino acids has been described. The reaction of N ^α -urethane-protected amino alkyl isocyanates with selenating agent LiAlHSeH and subsequent coupling with an alkyl halide yielded the title compounds in good yield and purity. All the selenocarbamates obtained have been characterized by ¹H NMR, ¹³C NMR, and mass spectral studies.

Keywords:

• LiAlHSeH
• N ^α -protected amino alkyl isocyanates
• selenium
• selenocarbamates

ACKNOWLEDGMENTS

The authors thank the Department of Science and Technology (Grant No. SR/S1/OC-26/2008) and the Council of Scientific and Industrial Research, Government of India, for financial support.

Notes

^a Corresponds to ES-MS of the compound.