Direct synthesis of Z, BOC, FMOC, ALLOC... Derivatives of 5- aminooxazoles starting from acylamino acids and chlorosulfonylcarbamates

Article abstract of DOI:10.1080/00397910008087418

A one-step synthesis of 5-oxazolecarbamates 1-11 can be easily carried out starting from N-acetylated and benzoylated aminoacids such as Gly, Ala, Leu, Phe, and chlorosulfonyl carbamates, prepared in situ by addition of alcohols on chlorosulfonyl isocyanate (CSI). The structure of the compounds was confirmed by X-Ray crystallography. A subsequent exocyclic N-alkylation gave substituted 12. 18 derivatives. Carbamate cleavage gave by spontaneous reopening substituted N-acylaminoamides, in excellent yields.

Full text of DOI:10.1080/00397910008087418

This article was downloaded by: [University of Pennsylvania]
On: 26 September 2013, At: 04:43
Publisher: Taylor & Francis
Informa Ltd Registered in England and Wales Registered Number: 1072954
Registered office: Mortimer House, 37-41 Mortimer Street, London W1T 3JH,
UK
Synthetic Communications: An
International Journal for Rapid
Communication of Synthetic
Organic Chemistry
Publication details, including instructions for
authors and subscription information:
http://www.tandfonline.com/loi/lsyc20
Direct Synthesis of Z, Boc,
Fmoc, Alloc[ddot] Derivatives
of 5-Aminooxazoles Starting
from Acylamino Acids and
Chlorosulfonylcarbamates
a b
a b
Georges Dewynter
, A. Houssem Hajri
, Loic
c
a b
Toupet & Jean-Louis Montero
a
Laboratoire de Chimie Biomoléculaire-UMR 5032,
F-34095, Montpellier
b
Université Montpellier-II, F-34095, Montpellier
c
G.M.C.M-UMR 6626. Université Rennes-I, F-35042,
Rennes
Published online: 04 Dec 2007.
To cite this article: Georges Dewynter , A. Houssem Hajri , Loic Toupet & Jean-
Louis Montero (2000) Direct Synthesis of Z, Boc, Fmoc, Alloc[ddot] Derivatives of
5-Aminooxazoles Starting from Acylamino Acids and Chlorosulfonylcarbamates,
Synthetic Communications: An International Journal for Rapid Communication of
Synthetic Organic Chemistry, 30:14, 2541-2548, DOI: 10.1080/00397910008087418
To link to this article: http://dx.doi.org/10.1080/00397910008087418
PLEASE SCROLL DOWN FOR ARTICLE

Taylor & Francis makes every effort to ensure the accuracy of all the
information (the “Content”) contained in the publications on our platform.
However, Taylor & Francis, our agents, and our licensors make no
representations or warranties whatsoever as to the accuracy, completeness,
or suitability for any purpose of the Content. Any opinions and views
expressed in this publication are the opinions and views of the authors, and
are not the views of or endorsed by Taylor & Francis. The accuracy of the
Content should not be relied upon and should be independently verified with
primary sources of information. Taylor and Francis shall not be liable for any
losses, actions, claims, proceedings, demands, costs, expenses, damages,
and other liabilities whatsoever or howsoever caused arising directly or
indirectly in connection with, in relation to or arising out of the use of the
Content.
This article may be used for research, teaching, and private study purposes.
Any substantial or systematic reproduction, redistribution, reselling, loan,
sub-licensing, systematic supply, or distribution in any form to anyone is
expressly forbidden. Terms & Conditions of access and use can be found at
http://www.tandfonline.com/page/terms-and-conditions