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Triethylamine → 3-(3-Chloropropylsulfonylamino)-2-methoxy-1-octadecylcarbamoylthiopropane

HRID 728431
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 728431
[CH3:1][O:2][CH:3]([CH2:6][S:7][C:8](=[O:28])[NH:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH2:4][NH2:5].C(N(CC)CC)C.[Cl:36][CH2:37][CH2:38][CH2:39][S:40](Cl)(=[O:42])=[O:41]>ClCCl.O1CCCC1>[Cl:36][CH2:37][CH2:38][CH2:39][S:40]([NH:5][CH2:4][CH:3]([O:2][CH3:1])[CH2:6][S:7][C:8](=[O:28])[NH:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])(=[O:42])=[O:41]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 154103-Chloropropanesulphonyl chlorideHCID 149922632-Methoxy-3-octadecylcarbamoylthiopropylamine

Produkt 1

HCID 148350333-(3-Chloropropylsulfonylamino)-2-methoxy-1-octadecylcarbamoylthiopropaneAusbeute 67 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344Dichloromethane
Lösungsmittel
2×
HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 93 mg (0.223 mM) of 2-methoxy-3-octadecylcarbamoylthiopropylamine IVa6 and 40.4 μl (3.9 mM) of triethylamine in 5 ml of dichloromethane and 2 ml of tetrahydrofuran is added 29.8 μl (3.3 mM) of 3-chloropropanesulfonyl chloride with ice-cooling, and the mixture is stirred for 2 hours and at room temperature for an additional 30 minutes. The product is isolated by dichloromethane extraction and the dichloromethane layer is washed with an aqueous sodium hydrogencarbonate and a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, and evaporated. The residue is purified by the column chromatography on silica gel with a benzene-ethyl acetate (4:1) mixture as an eluent to give 83 mg (0.149 mM) of 3-(3-chloropropylsulfonylamino)-2-methoxy-1-octadecylcarbamoylthiopropane IIIa6 as a colorless powder in 67% yield.

Aufarbeitung

  1. temperaturecooling
  2. washthe dichloromethane layer is washed with an aqueous sodium hydrogencarbonate
  3. dry with materiala saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate
  4. customevaporated
  5. customThe residue is purified by the column chromatography on silica gel with a benzene-ethyl acetate (4:1) mixture as an eluent

Quellen und Nachweise

ORD-Eintrag
ord-1a64c8eebad84b0088983d6d07db2990
Quelldatensatz
uspto-grants-1991_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05047540

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