Rapid Procedure for N-Phthaloylation of α-Amino Carboxamides, α-Amino Alcohols, α-Amino Esters and Dipeptide Derivatives

J. Richard Casimir; Gilles Guichard; Dirk Tourwé; Jean-Paul Briand

doi:10.1055/s-2001-17710

PAPER

Rapid Procedure for N-Phthaloylation of α-Amino Carboxamides, α-Amino Alcohols, α-Amino Esters and Dipeptide Derivatives

J. Richard Casimir*^a, Gilles Guichard^a, Dirk Tourwé^b, Jean-Paul Briand^a
^a Laboratoire de Chimie Immunologique, UPR 9021 CNRS (IBMC), 15 rue René Descartes, 67084 Strasbourg cedex, France
^b Department of Organic Chemistry, Vrije Universiteit Brussel (VUB), Pleinlaan 2, 1050 Brussels, Belgium
Fax: +33(3)88610680; e-Mail: CASIMIR.Richard@wanadoo.fr;

Abstract

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Abstract

A rapid, one-pot synthesis and mild procedure for the N-phthaloylation of α-amino carboxamides is described. In acetonitrile, these derivatives react with mono-methylphthalate in the presence of BOP and i-Pr₂NEt to afford the intermediate N ^α-[(o-methoxycarbonyl)benzoyl]amino carboxamides, which undergo rapid cyclization in the presence of aqueous sodium carbonate to afford the corresponding N ^α-phthaloylamino carboxamides in excellent yields. The reaction also works efficiently with α-amino esters, α-amino alcohols and dipeptide esters or amides.

Key words

phthaloyl protection - α-amino carboxamides - mono-methylphthalate - α-amino alcohols - cyclization

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References

<A NAME="RZ05001SS-1">1</A> Kukolja S. Lammert SR. J. Am. Chem. Soc. 1975, 97: 5582

<A NAME="RZ05001SS-2">2</A> Schumann I. Boissonnas RA. Helv. Chim. Acta. 1952, 35: 2235

<A NAME="RZ05001SS-3">3</A> Sheehan JC. Chapman DW. Roth RW. J. Am. Chem. Soc. 1952, 74: 3822

<A NAME="RZ05001SS-4">4</A> Casimir JR. Guichard G. Briand J.-P. Synthesis 2001, 75

<A NAME="RZ05001SS-5">5</A> Billman JH. Harting WF. J. Am. Chem. Soc. 1948, 70: 1473

<A NAME="RZ05001SS-6">6</A> Nefkens GHL. Tesser GI. Nivard RJF. Recl. Trav.Chim. Pays-Bas 1960, 79: 688

<A NAME="RZ05001SS-7">7</A> McArthur CR. Worster PM. Okon AU. Synth. Commun. 1983, 13: 311

<A NAME="RZ05001SS-8">8</A> Hoogwater DA. Reinhoudt DN. Lie TS. Gunneweg JJ. Beyerman HG. Recl. Trav.Chim. Pays-Bas 1973, 92: 819

<A NAME="RZ05001SS-9">9</A> Sheehan JC. Goodman M. Hess G. J. Am. Chem. Soc. 1956, 78: 1367

<A NAME="RZ05001SS-10">10</A> Reddy PY. Kondo S. Toru T. Ueno Y. J. Org. Chem. 1997, 62: 2652

<A NAME="RZ05001SS-11">11</A> Aguilar N. Moyano A. Pericàs MA. Riera A. Synthesis 1998, 313

<A NAME="RZ05001SS-12">12</A> Damm W. Hoffmann U. Macko L. Neuburger M. Zehnder M. Giese B. Tetrahedron 1994, 50: 7029

<A NAME="RZ05001SS-13">13</A> Fling M. Minard FN. Fox SW. J. Am. Chem. Soc. 1947, 69: 2466

<A NAME="RZ05001SS-14">14</A> Shealy YF. Opliger CE. Montgomery JA. J. Pharm. Sci. 1968, 57: 757

<A NAME="RZ05001SS-15">15</A> Sato H. Kusumi T. Imaye K. Kakisawa H. Bull. Chem. Soc. Jpn. 1976, 49: 2815

<A NAME="RZ05001SS-16">16</A> Hoffmann E. Schiff-Shenhav H. J. Org. Chem. 1962, 27: 4686

<A NAME="RZ05001SS-17">17</A> Worster PM. Leznoff CC. McArthur CR. J. Org. Chem. 1980, 45: 174

<A NAME="RZ05001SS-18">18</A> Adriaens P. Meesschaert B. Janssen G. Dumon L. Eyssen H. Recl. Trav. Chim. Pays-Bas. 1978, 97: 260

<A NAME="RZ05001SS-19">19</A> Wicks ZWJr. Chen G.-F. J. Org. Chem. 1979, 44: 1244

<A NAME="RZ05001SS-20">20</A> Casimir JR. Tourwé D. Iterbeke K. Guichard G. Briand J.-P. J. Org. Chem. 2000, 65: 6487

<A NAME="RZ05001SS-21">21</A> Casimir JR. Iterbeke K. van den Nest W. Trescol-Biémont M.-C. Dumortier H. Muller S. Gerlier D. Rabourdin-Combe C. Tourwé D. Paris J. J. Peptide Res. 2000, 56: 398

<A NAME="RZ05001SS-22">22</A> Nimura N. Ogura H. Kinoshita T. J. Chromatogr. 1980, 202: 375

In both cases, the ratio l/d was >99:1.

<A NAME="RZ05001SS-24">24</A> Tyler AN. Clayton E. Green BN. Anal. Chem. 1996, 68: 3561