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Synthesis 1996; 1996(11): 1355-1358
DOI: 10.1055/s-1996-4396
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Facile Synthesis of 1-Adamantyl Esters of L-α-Amino Acids, a New Class of Carboxy Protected Derivatives

Stella M. Iossifidou, Cleanthis C. Froussios*
  • *Laboratory of Organic Chemistry, Chemistry Department, University of Athens, University Campus, Zografou, 15771 Athens, Greece, Fax +30(1)7249101; E-mail organic@arnold.phchem.uoa.ariadne-t.gr
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Publication Date:
31 December 2000 (online)

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1-Adamantyl esters of several N-unprotected L-α-amino acids were directly prepared in good optical purity and yield by reaction of the corresponding amino acid 4-toluenesulfonate salts with 1-adamantanol (AdOH) and dimethyl sulfite in boiling toluene. The fully protected tripeptide Boc-Leu-Ala-Val-OAd, prepared from TsOH.H-Val-OAd (entry 2b) was amino deprotected to H-Leu-Ala-Val-OAd by the action of 4N HCl in dioxane for 25 minutes at 20°C, while the latter was carboxy deprotected to the free peptide by the action of trifluoroacetic acid for 60 minutes at 20°C. The 1-adamantyl ether of threonine (5) was also prepared and the 1-adamantyl moiety was completely cleaved from Troc-Thr(OAd)-OH by the action of trifluoroacetic acid for 30 minutes at 20°C.

1-adamantanol - α-amino acid esterification - dimethyl sulfite - threonine 1-adamantyl ether

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