Triethylamine → 6-(Pyridine-3-sulfonylamino)hexanoic acid methyl ester

HRID 351094

Reaktionsgleichung

Reaktionsgleichung von HRID 351094
Cl.[N:2]1[CH:7]=[CH:6][CH:5]=[C:4]([S:8](Cl)(=[O:10])=[O:9])[CH:3]=1.Cl.[NH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([O:21][CH3:22])=[O:20].C(N(CC)CC)C>C(#N)C>[CH3:22][O:21][C:19](=[O:20])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][NH:13][S:8]([C:4]1[CH:3]=[N:2][CH:7]=[CH:6][CH:5]=1)(=[O:10])=[O:9]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 11499324Methyl 6-aminohexanoate hydrochlorideHCID 12571517Pyridine-3-sulfonyl chloride hydrochloride

Produkt 1

HCID 207804896-(Pyridine-3-sulfonylamino)hexanoic acid methyl esterAusbeute 76,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

Pyridine-3-sulfonyl chloride hydrochloride (92c) (1.8 g, 5.0 mmol) was added to a solution of methyl 6-aminohexanoate hydrochloride (91) (1.82 g, 10 mmol) and triethylamine (3.03 g, 30 mmol) in acetonitrile (30 ml). The mixture was stirred for 1 hour at ambient temperature, filtered and solvents were removed under reduced pressure. The oily product was dissolved in water (15 ml) and extracted with ethyl ether (50 ml). The extract was dried (Na2SO4) and the solvents were removed under reduced pressure. The title compound (1.09 g, 76%) was obtained as oil and was used for the next step without an additional purification. 1H NMR δH (90 MHz, DMSO-d6) δ: 0.80–1.51 (6H, m, CH2); 1.83 (2H, t, J=6.5 Hz, CH2); 2.76 (2H, t, J=6.5 Hz, CH2N); 3.58 (3H, s, CH3); 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).

Aufarbeitung

  1. filtrationfiltered
  2. customsolvents were removed under reduced pressure
  3. dissolutionThe oily product was dissolved in water (15 ml)
  4. extractionextracted with ethyl ether (50 ml)
  5. dry with materialThe extract was dried (Na2SO4)
  6. customthe solvents were removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-133fc99d50ea4e698a1a76b5839a0204
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07183298B2

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