O-Protected N-(2-Nitrophenylsulfonyl)hydroxylamines: Novel Reagents for the Synthesis of Hydroxamates

Poreddy Amruta Reddy; Otto F. Schall; James R. Wheatley; Leonard O. Rosik; Joseph P. McClurg; Garland R. Marshall; Urszula Slomczynska

doi:10.1055/s-2001-14567

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Synthesis 2001(7): 1086-1092
DOI: 10.1055/s-2001-14567

PAPER

O-Protected N-(2-Nitrophenylsulfonyl)hydroxylamines: Novel Reagents for the Synthesis of Hydroxamates

Poreddy Amruta Reddy^a, Otto F. Schall^a, James R. Wheatley^a, Leonard O. Rosik^a, Joseph P. McClurg^a, Garland R. Marshall^a,b, Urszula Slomczynska*^a
^a MetaPhore Pharmaceuticals, Inc., 1910 Innerbelt Business Service Center Drive, Saint Louis, MO 63114, USA
Fax: +1(314)4267491; e-Mail: uslomczynska@metaphore.com;
^b Department of Biochemistry and Molecular Biophysics, Washington University School of Medicine, 660 South Euclid Avenue, Saint Louis, MO 63110, USA

Further Information

Publication History

Received 12 January 2001
Publication Date:
30 September 2004 (online)

Abstract
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Abstract

Preparative methods for novel O-protected N-(2-nitrophenylsulfonyl)hydroxylamines (8a-e) are described. Their versatility as intermediates en route to polyhydroxamates is exemplified by the synthesis of a non-amide DFO analog 22.

Key words

hydroxamate - nosyl protecting group - solid-phase synthesis - alkylation - Mitsunobu reaction

References

1 Bickel H. Hall GE. Keller-Schierlein W. Prelog V. Vischer E. Wettstein A. Helv. Chim. Acta 1960, 43: 2129

Crossref Google Scholar
2 Olivieri NF. Brittenham GM. Blood 1997, 89: 739

Google Scholar
3 Bergeron RJ. Wiegand J. McManis JS. Perumal PT. J. Med. Chem. 1991, 34: 3182

Crossref Google Scholar
4 Bergeron RJ. McManis JS. Phanstiel IVO. Vinson JRT. J. Org. Chem. 1995, 60: 109

Google Scholar
5 Dionis JB. Jenny H.-B. Peter HH. J. Org. Chem. 1989, 54: 5623

Google Scholar
6 Bergeron RJ. Liu Z.-R. McManis JS. Weigand J. J. Med. Chem. 1992, 35: 4739

Crossref Google Scholar
7 Fukuyama T. Jow C.-K. Cheung M. Tetrahedron Lett. 1995, 36: 6373

Crossref Google Scholar
8 Fukuyama T. Cheung M. Jow C.-K. Hidai Y. Kan T. Tetrahedron Lett. 1997, 38: 5831

Crossref Google Scholar
9 Bhatt U. Mohamed N. Just G. Tetrahedron Lett. 1997, 38: 3679

Crossref Google Scholar
10 Bowman WR. Coghlan DR. Tetrahedron 1997, 53: 15787

Crossref Google Scholar
11 Miller SC. Scanlan TS. J. Am. Chem. Soc. 1997, 119: 2301

Crossref Google Scholar
12 Miller SC. Scanlan TS. J. Am. Chem. Soc. 1998, 120: 2690

Crossref Google Scholar
13 Reichwein JF. Liskamp RMJ. Tetrahedron Lett. 1998, 39: 1243

Crossref Google Scholar
14 Greene TW. Wutts PGM. Protective Groups in Organic Synthesis Wiley; New York: 1999. p.17

Google Scholar
15 Barlaam B. Hamon A. Maudet M. Tetrahedron Lett. 1998, 39: 7865

Crossref Google Scholar
16 Altenburger JM. Mioskowski C. d"Orchymont H. Schirlin D. Schalk C. Tarnus C. Tetrahedron Lett. 1992, 33: 5055

Crossref Google Scholar
17 Singha AS. Misra BN. Indian J. Chem. 1982, 21B: 361

Google Scholar
18 Conway TT. DeMaster EG. Goon DJW. Shirota FN. Nagasawa HT. J. Med. Chem. 1999, 42: 4016

Crossref Google Scholar
20 Patel DV. Young MG. Robinson SP. Hunihan L. Dean BJ. Gordon EM. J. Med. Chem. 1996, 39: 4197

Crossref Google Scholar
22 Wilson MW. Ault-Justus SE. Hodges JC. Rubin JR. Tetrahedron 1999, 55: 1647

Crossref Google Scholar
23 Wuts PGM. Northuis JM. Tetrahedron Lett. 1998, 39: 3889

Crossref Google Scholar
24 Rich DH. Singh J. Gardner JH. J. Org. Chem. 1983, 48: 432

Google Scholar
25 Slomczynska U. Reddy PA. Schall O. Rosik L. Wheatley JW. Marshall GR. Transfusion Science 2000, 23: 265

Crossref Google Scholar

19

N-Bis(2-nitrophenylsulfonyl)-O-(phenylmethyl)-hydroxylamine: ¹H NMR (DMSO-d ₆): δ = 8.17-8.07 (m, 6 H), 7.97-7.91 (m, 2 H), 7.39-7.34 (m, 3 H), 7.24-7.22 (m, 2 H), 4.96 (s, 2 H).

21

N-Bis(4-nitrophenylsulfonyl)-O-(phenylmethyl)-hydroxylamine [¹H NMR (DMSO-d ₆): δ = 10.90 (s, 1 H), 8.47 (d, 2 H, J = 8.8 Hz), 8.15 (d, 2 H, J = 8.8 Hz), 7.45-7.30 (m, 5 H), 4.94 (s, 2 H)] from 6a and O-(1,1-Dimethylethyl)-N-(4-nitrophenylsulfonyl)hydroxylamine [¹H NMR (DMSO-d ₆): δ = 10.21 (s, 1H), 8.46 (d, 2H, J = 8.8 Hz), 8.09 (d, 2H, J = 8.8 Hz), 1.17 (s, 9H)] from 6c.

26

Compound with trace impurities was found to decompose at r. t. over time. Once purified, it can be stored in the refrigerator indefinitely.

27

It is critical that the first 125-mL portion not be shaken, but rather gently mixed and then separated. This will ensure the separation of layers even after shaking well during all subsequent extractions.