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

Research output: Contribution to journal › Article › peer-review

58 Scopus citations

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.

Publisher link

10.1016/0040-4039(96)00589-8

Find It

Find It at U of M Libraries

Cite this

@article{ce1b399814d44a6a9b61f252f0317305,

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

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.",

author = "Khalil, {Ehab M.} and Subasinghe, {Nalin L.} and Johnson, {Rodney L.}",

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.",

year = "1996",

month = may,

day = "13",

doi = "10.1016/0040-4039(96)00589-8",

language = "English (US)",

volume = "37",

pages = "3441--3444",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Ltd",

number = "20",

}

TY - JOUR

T1 - An efficient and high yield method for the N-tert-butoxycarbonyl protection of sterically hindered amino acids

AU - Khalil, Ehab M.

AU - Subasinghe, Nalin L.

AU - Johnson, Rodney L.

N1 - Funding Information: This work was supportebdyan NIH grant( NS20036t)o R.L.J. We thankP .W. Banresf or providings amples of compoundlsa and ld.

PY - 1996/5/13

Y1 - 1996/5/13

N2 - 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.

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.

UR - http://www.scopus.com/inward/record.url?scp=0029945520&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0029945520&partnerID=8YFLogxK

U2 - 10.1016/0040-4039(96)00589-8

DO - 10.1016/0040-4039(96)00589-8

M3 - Article

AN - SCOPUS:0029945520

SN - 0040-4039

VL - 37

SP - 3441

EP - 3444

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 20

ER -

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

Abstract

Bibliographical note

Publisher link

Find It

Other files and links

Fingerprint

Cite this