Deprotection of o-Nitrobenzensulfonyl (Nosyl) Derivatives of Amines ­Mediated by a Solid-Supported Thiol

Francesca Cardullo; Daniele Donati; Giancarlo Merlo; Alfredo Paio; Margherita Salaris; Maurizio Taddei

doi:10.1055/s-2005-921892

LETTER

Deprotection of o-Nitrobenzensulfonyl (Nosyl) Derivatives of Amines Mediated by a Solid-Supported Thiol

Francesca Cardullo^a, Daniele Donati^a, Giancarlo Merlo^a, Alfredo Paio^a, Margherita Salaris^b, Maurizio Taddei*^c
^a GlaxoSmithKline, Med. Res. Centre, Via A. Fleming 4, 37135 Verona, Italy
^b Dipartimento di Chimica, Università degli Studi di Sassari, Via Vienna 2, 07100 Sassari, Italy
^c Dipartimento Farmaco Chimico Tecnologico, Università degli Studi di Siena, Via A. Moro, 53100 Siena, Italy
Fax: +39(0577)234275; e-Mail: taddei.m@unisi.it;

Abstract

All articles of this category

Abstract

A new protocol based on a solid-supported thiol was developed for high yielding deprotection of o-nitrobenzensulfonyl amides derived from primary and secondary amines. The reaction can be carried out at room temperature for 24 hours or accelerated by microwave irradiation, going to completion in six minutes.

Key words

solid-supported reagents - amines - protecting groups - microwaves

Full Text

References

1a Bhattacharyya S. Curr. Opin. Drug Discov. Devel. 2004, 7: 752

1b Hodge P. Curr. Opin. Chem. Biol. 2003, 7: 362

1c Ley SV. Baxendale IR. Nat. Rev. Drug Discov. 2002, 1: 573

1d Flynn DL. Berk SC. Makara GM. Curr. Opin. Drug Discov. Devel. 2002, 5: 580

1e

Janda, K. (Ed.) Bioorg. Med. Chem. Lett. 2002, 12(14).

1f Kirschning A. Monenschein H. Wittemberg R. Angew. Chem. Int. Ed. 2001, 40: 650

2a Hodge P. Curr. Opin. Chem. Biol. 2003, 7: 362

2b Sherrington DC. J. Polym. Sci., Part A: Polym. Chem. 2001, 39: 2364

2c Shuttleworth SJ. Allin SM. Wilson RD. Nasturica D. Synthesis 2000, 1035

2d Booth RJ. Hodges JC. Acc. Chem. Res. 1999, 32: 18

3a Ley SV. Baxendale IR. Bream RN. Jackson PS. Leach AG. Longbottom DA. Nesi M. Scott JS. Storer RI. Taylor SJ. J. Chem. Soc., Perkin Trans. 1 2000, 3815

For the most recent research reports on the argument see:

3b Ploypradith P. Kagan RK. Ruchiravat S. J. Org. Chem. 2005, 70: 5119

3c Gendre F. Yang M. Diaz P. Org. Lett. 2005, 7: 2719

3d Brenelli ECS. Brenelli JA. Pinto RCL. Tetrahedron 2005, 61: 5323

3e Ghiron C. Nannetti L. Taddei M. Tetrahedron Lett. 2005, 46: 1643

3f Donati D. Morelli C. Taddei M. Tetrahedron Lett. 2005, 46: 2817

3g Desai B. Danks TN. Wagner G. Tetrahedron Lett. 2005, 46: 955

3h Heriksen HS. Cotes Oyaga S. Sherrington DC. Gibson CL. Synlett 2005, 1235

4a Dondoni A. Marra A. Massi A. Angew. Chem. Int. Ed. 2005, 44: 1672

4b Chari MA. Syamasundar K. Synthesis 2005, 708

4c Baxendale IR. Ernst M. Krahnert W.-R. Ley SV. Synlett 2002, 1641

4d Hon Y.-S. Lee C.-F. Chen R.-J. Szu P.-H. Tetrahedron 2001, 57: 5991

4e Sheppeck JE. Kar H. Hong H. Tetrahedron Lett. 2000, 41: 5329

5 Green TW. Wuts PGM. Protective Groups in Organic Synthesis 3rd ed.: J. Wiley and Sons; New York: 1999. p.610

6a Fukuyama T. Jow C.-K. Cheung M. Tetrahedron Lett. 1995, 36: 6373

6b Maligres PE. See MM. Askin D. Reider PJ. Tetrahedron Lett. 1997, 38: 5235

7 Deprotection of nosylamides using fluorous reagents followed by selective solid-phase extraction has been reported: Christensen C. Clausen RP. Begtrup M. Kristensen JL. Tetrahedron Lett. 2004, 45: 7991

8a Schneider MR. Mann A. Taddei M. Tetrahedron Lett. 1996, 37: 8493

8b Ungureanu I. Bologa C. Chayer S. Mann A. Tetrahedron Lett. 1999, 40: 5315

9

Commercially available form Aldrich or Argonaut.

10 Commercially available from Novabiochem. See also: Parrott I. Wermuth C.-W. Hibert M. Tetrahedron Lett. 1999, 40: 7975

Deprotection of o-Nitrobenzensulfonyl (Nosyl) Derivatives of Amines ­Mediated by a Solid-Supported Thiol

Deprotection of o-Nitrobenzensulfonyl (Nosyl) Derivatives of Amines Mediated by a Solid-Supported Thiol