Hydroxylamine → N-hydroxy-{N-[2-(cyclopentyl)ethyl]-N-[2-(3-hydroxyphenyl)aminocarbonylpyrrolidin-1-ylcarbonyl]-amino}acetamide

HRID 23596Notes

Reaction equation

HRID 23596 reaction equation
[CH:1]1([CH2:6][CH2:7][N:8]([CH2:26][C:27]([O:29]CC)=O)[C:9]([N:11]2[CH2:15][CH2:14][CH2:13][CH:12]2[C:16]([NH:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([OH:25])[CH:20]=2)=[O:17])=[O:10])[CH2:5][CH2:4][CH2:3][CH2:2]1.[NH2:32][OH:33]>O1CCOCC1>[OH:33][NH:32][C:27](=[O:29])[CH2:26][N:8]([CH2:7][CH2:6][CH:1]1[CH2:2][CH2:3][CH2:4][CH2:5]1)[C:9]([N:11]1[CH2:15][CH2:14][CH2:13][CH:12]1[C:16]([NH:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([OH:25])[CH:20]=1)=[O:17])=[O:10]

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 22575075HCID 22575075, compound

Product 1

HCID 22575066N-hydroxy-{N-[2-(cyclopentyl)ethyl]-N-[2-(3-hydroxyphenyl)aminocarbonylpyrrolidin-1-ylcarbonyl]-amino}acetamide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To ethyl 2-[N-(2-(cyclopentyl)ethyl)-N-[2-(3-hydroxyphenyl)aminocarbonyl-pyrrolidin-1-carbonyl)amino]acetate (200 μmol) in dioxane (2 mL) was added 50% aqueous hydroxylamine (1 mL), and the reaction stirred for 36 h. The crude reaction mixture was then purified by preparative reverse-phase (C18) HPLC to afford N-hydroxy-{N-[2-(cyclopentyl)ethyl]-N-[2-(3-hydroxyphenyl)aminocarbonylpyrrolidin-1-ylcarbonyl]-amino}acetamide. 1H NMR (DMSO-d6): δ9.33 (br s, 1H), 7.25-7.24 (m, 1H), 7.07-6.99 (m, 2H), 6.45-6.41 (m, 1H), 4.38 (dd, J=8.4, 8.4, 1H), 3.88 (d, J=16.5, 1H), 3.66 (d, J=16.5, 1H), 3.48-3.46 (m, 2H), 3.27-3.22 (m, 1H), 3.20-3.01 (m, 1H), 2.19 (br s, 1H), 1.91 (br s, 1H), 1.73-1.68 (m, 5H), 1.63-1.41 (m, 6H), 1.08-1.05 (m, 2H). ES−MS: calcd. for C21H30N4O5 (418.2); found: 417.7 [M−1].

Workup

  1. customThe crude reaction mixture
  2. customwas then purified by preparative reverse-phase (C18) HPLC

Sources & evidence

ORD record
ord-26df486bcc5b43f0b42bbae94a0f3902
Source dataset
uspto-grants-2005_02
Patent number
US06852752B2

Reaction notes

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