Triethylamine → 3-(4-Chlorobutylsulfonylamino)-2-methoxy-1-octadecylcarbamoyloxypropane

HRID 728428

Reaktionsgleichung

Reaktionsgleichung von HRID 728428
[CH3:1][O:2][CH:3]([CH2:6][O: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][CH2:40][S:41](Cl)(=[O:43])=[O:42]>ClCCl>[Cl:36][CH2:37][CH2:38][CH2:39][CH2:40][S:41]([NH:5][CH2:4][CH:3]([O:2][CH3:1])[CH2:6][O: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:43])=[O:42]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 742124-Chlorobutane-1-sulphonyl chlorideHCID 149922622-Methoxy-3-octadecylcarbamoyloxypropylamine

Produkt 1

HCID 148350313-(4-Chlorobutylsulfonylamino)-2-methoxy-1-octadecylcarbamoyloxypropaneAusbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel3×

Versuchsvorschrift

To a solution of 1.2 g (3 mM) of 2-methoxy-3-octadecylcarbamoyloxypropylamine IVa1 in 24 ml of dichloromethane and 0.5 ml (3.6 mM) of triethylamine is added 0.75 g (3.93 mM) of 4-chlorobutanesulfonyl chloride with ice-cooling and the mixture is stirred at room temperature overnight. The product is isolated with dichloromethane extraction and dichloromethane layer is washed with saturated aqueous sodium hydrogencarbonate and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and evaporated. The residue is purified by the column chromatography on silica gel with a n-hexane-ethyl acetate (3:2) mixture as an eluent. The product is recrystallized from dichloromethane-n-hexane to give 1.28 g (2.305 mM) of 3-(4-chlorobutylsulfonylamino)-2-methoxy-1-octadecylcarbamoyloxypropane IIIa5 as colorless crystals in 77% yield.

Aufarbeitung

  1. temperaturecooling
  2. washis washed with saturated aqueous sodium hydrogencarbonate and saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated
  5. customThe residue is purified by the column chromatography on silica gel with a n-hexane-ethyl acetate (3:2) mixture as an eluent
  6. customThe product is recrystallized from dichloromethane-n-hexane

Quellen und Nachweise

ORD-Eintrag
ord-3eaddd452a6a4961beaa3b84ccbf49b8
Quelldatensatz
uspto-grants-1991_09
Patentnummer
US05047540

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