Oxalic Acid → 6-(Pyridine-3-sulfonylamino)hexanoic acid hydroxyamide oxalate

HRID 226189

Reaction equation

HRID 226189 reaction equation
C[O-].[Na+].Cl.[NH2:5][OH:6].[Na+].[Cl-].C[O:10][C:11](=O)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][NH:17][S:18]([C:21]1[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=1)(=[O:20])=[O:19].[C:28]([OH:33])(=[O:32])[C:29]([OH:31])=[O:30]>CO>[C:28]([OH:33])(=[O:32])[C:29]([OH:31])=[O:30].[OH:6][NH:5][C:11](=[O:10])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][NH:17][S:18]([C:21]1[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=1)(=[O:20])=[O:19]

Participants

7

Reactant 5

HCID 971Oxalic AcidHCID 5234Sodium ChlorideHCID 443297Hydroxyamine hydrochlorideHCID 10942334Sodium MethoxideHCID 207804896-(Pyridine-3-sulfonylamino)hexanoic acid methyl ester

Product 1

HCID 865919036-(Pyridine-3-sulfonylamino)hexanoic acid hydroxyamide oxalateYield 44%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of sodium methylate (12 mmol) in methanol (10 ml) was added to a solution of hydroxylamine hydrochloride (0.56 g, 8 mmol) in methanol (16 ml). The mixture was stirred for 10 min, and NaCl was filtered off 6-(Pyridine-3-sulfonylamino)hexanoic acid methyl ester (93c) (0.58 g, 2 mmol) was added to the filtrate and the mixture was left to stand overnight at ambient temperature. The precipitate was filtered off, dissolved in water (20 ml) and oxalic acid (0.36 g, 4 mmol) was added to the solution. Water was removed under reduced pressure and the product was crystallised from methanol. The title compound (0.33 g, 44%) was obtained as white solid. M.p. 132-134° C. 1H NMR δH. (90 MHz, DMSO-d6) δ: 0.78-1.49 (6H, m, CH2), 1.83 (2H, t, J=6.5 Hz, CH2); 2.76 (2H, t, J=6.5 Hz, CH2N); 7.54 (1H, dd, J=5.0 Hz, J=8.2 Hz, C5HN); 8.12 (1H, dt, J=2.0 Hz, J=8.2 Hz, C5HN); 8.61 (1H, dd, J=2.0 Hz, J=5.0 Hz, C5HN); 8.81 (1H, d, J=2.0 Hz, C5HN). HPLC analysis on Symmetry C18 column: impurities <1% (column size 3.9×150 mm; mobile phase acetonitrile—0.1M phosphate buffer (pH 2.5), 5: 95; detector UV 254 nm; sample concentration 1.0 mg/ml). Anal. Calcd for C11H17N3O4S*(COCH)2: C 41.38, H 5.07, N 11.13. Found: C 41.53, H 5.10, N 19.83.

Workup

  1. additionwas added to the filtrate
  2. waitthe mixture was left
  3. waitto stand overnight at ambient temperature
  4. filtrationThe precipitate was filtered off
  5. dissolutiondissolved in water (20 ml)
  6. customWater was removed under reduced pressure
  7. customthe product was crystallised from methanol

Sources & evidence

ORD record
ord-f8b0131305ac413bb702d741917e569a
Source dataset
uspto-grants-2009_07
Patent number
US07557140B2

Linked notes

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