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

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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.