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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 40, 2010 - Issue 18
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Original Articles

Synthesis of Nα-Protected Amino Acid–Derived Selenocarbamates Employing Isocyanates as Key Intermediates

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Pages 2676-2685 | Received 01 Jun 2009, Published online: 09 Aug 2010
 

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.

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.

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