Sodium Hydroxide → HCID 131724844, compound

HRID 1816550Notes

Reaction equation

HRID 1816550 reaction equation
C([O:8][NH:9][C:10](=[O:27])[CH2:11][CH2:12][CH:13]([C:24]([OH:26])=[O:25])[CH2:14][C:15]1[CH:23]=[CH:22][C:18]([C:19]([OH:21])=[O:20])=[CH:17][CH:16]=1)C1C=CC=CC=1.[OH-].[Na+:29]>[Pd].O>[Na+:29].[Na+:29].[C:24]([CH:13]([CH2:12][CH2:11][C:10]([NH:9][OH:8])=[O:27])[CH2:14][C:15]1[CH:16]=[CH:17][C:18]([C:19]([O-:21])=[O:20])=[CH:22][CH:23]=1)([OH:26])=[O:25].[C:24]([CH:13]([CH2:12][CH2:11][C:10](=[O:27])[NH:9][OH:8])[CH2:14][C:15]1[CH:16]=[CH:17][C:18]([C:19]([O-:21])=[O:20])=[CH:22][CH:23]=1)([OH:26])=[O:25]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 22494977HCID 22494977, compound

Product 1

HCID 131724844HCID 131724844, compoundYield 96.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

A 100-mL three neck round bottomed flask was charged with the 4-[5-(benzyloxyamino)-2-carboxy-5-oxopentyl]benzoic acid (0.500 g, 1.3 mmol), 0.5 N NaOH (5.2 mL, 2.6 mmol), water (8.3 ml), and a spatula full of 10% Pd on carbon. The mixture was stirred under hydrogen (1 atm) for 7 h. The catalyst was removed by filtration and the filtrate was lyophilized to give 0.382 g of 4-[2-carboxy-5-(hydroxyamino)-5-oxopentyl]benzoic acid disodium salt as an off white powder (89% yield): 1H NMR (D2O) δ 1.75-1.90 (m, 2H), 2.10-2.30 (m, 2H), 2.45-2.60 (m, 1H), 2.75-3.00 (m, 2H), 7.34 (d, J=8.0 Hz, 2H), 7.82 (d, J=8.0 Hz, 2H). Anal. Cacld. for C13H13NNa2O6.0.78H2O: C, 46.02; H, 4.33; N, 4.13. Found: C, 46.06; H, 4.14; N, 3.79.

Workup

  1. customThe catalyst was removed by filtration

Sources & evidence

ORD record
ord-cab0778ce81d4c6ba93bf89c2ce465c1
Source dataset
uspto-grants-2005_04
Patent number
US06884907B2

Reaction notes

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