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

HRID 351095

Reaktionsgleichung

Reaktionsgleichung von HRID 351095
C[O-].[Na+].Cl.[NH2:5][OH:6].C[O:8][C:9](=O)[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][NH:15][S:16]([C:19]1[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=1)(=[O:18])=[O:17].[C:26]([OH:31])(=[O:30])[C:27]([OH:29])=[O:28]>CO>[C:26]([OH:31])(=[O:30])[C:27]([OH:29])=[O:28].[OH:6][NH:5][C:9](=[O:8])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][NH:15][S:16]([C:19]1[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=1)(=[O:18])=[O:17]

Komponenten

6

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Versuchsvorschrift

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*(COOH)2: C, 41.38; H, 5.07; N, 11.13. Found: C, 41.53; H, 5.10; N, 19.83.

Aufarbeitung

  1. filtrationNaCl was filtered off
  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

Quellen und Nachweise

ORD-Eintrag
ord-1c56f6b395ed44ce9a9ec51852ad9644
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07183298B2

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