An efficient and high yield method for the N-tert-butoxycarbonyl protection of sterically hindered amino acids

Ehab M. Khalil; Nalin L. Subasinghe; Rodney L. Johnson

doi:10.1016/0040-4039(96)00589-8

An efficient and high yield method for the N-tert-butoxycarbonyl protection of sterically hindered amino acids

Ehab M. Khalil, Nalin L. Subasinghe, Rodney L. Johnson

Medicinal Chemistry

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Abstract

An important method for the N-tert-butoxycarbonyl protection of the amino functionality of α-alkylated prolines and other sterically hindered α,α-disubstituted amino acids has been developed in which the lipophilic base tetramethylammonium hydroxide is used to solubilize the otherwise insoluble zwitterionic amino acid in acetonitrile, thereby obviating the need for an aqueous medium.

Original language	English (US)
Pages (from-to)	3441-3444
Number of pages	4
Journal	Tetrahedron Letters
Volume	37
Issue number	20
DOIs	https://doi.org/10.1016/0040-4039(96)00589-8
State	Published - May 13 1996

Bibliographical note

Funding Information:
This work was supportebdyan NIH grant( NS20036t)o R.L.J. We thankP .W. Banresf or providings amples of compoundlsa and ld.

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AU - Subasinghe, Nalin L.

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AB - An important method for the N-tert-butoxycarbonyl protection of the amino functionality of α-alkylated prolines and other sterically hindered α,α-disubstituted amino acids has been developed in which the lipophilic base tetramethylammonium hydroxide is used to solubilize the otherwise insoluble zwitterionic amino acid in acetonitrile, thereby obviating the need for an aqueous medium.

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An efficient and high yield method for the N-tert-butoxycarbonyl protection of sterically hindered amino acids

Abstract

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