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3-Chloropropanesulphonyl chloride → 3-(3-Chloropropylsulfonylamino)-2-methoxy-1-octadecylcarbamoyloxypropane

HRID 846960
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 846960
[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].[Cl:29][CH2:30][CH2:31][CH2:32][S:33](Cl)(=[O:35])=[O:34]>ClCCl.C(N(CC)CC)C>[Cl:29][CH2:30][CH2:31][CH2:32][S:33]([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:35])=[O:34]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 154103-Chloropropanesulphonyl chlorideHCID 149922622-Methoxy-3-octadecylcarbamoyloxypropylamine

Produkt 1

HCID 148350183-(3-Chloropropylsulfonylamino)-2-methoxy-1-octadecylcarbamoyloxypropaneAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittel3×HCID 8471
Triethylamine
Lösungsmittel

Versuchsvorschrift

To a solution of 1.2 g (3 mM) of 2-methoxy-3-octadecylcarbamoyloxypropylamine IV a1 (described in JP Kokai No. 60-243047) in 24 ml of dichloromethane and 0.54 ml (3.9 mM) of triethylamine is added 0.401 ml (3.3 mM) of 3-chloropropanesulfonyl chloride with ice-cooling and the mixture is stirred at room temperature overnight. The product is isolated by 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 chloroform-n-hexane mixture to give 1.386 g (2.56 mM) of 3-(3-chloropropylsulfonylamino)-2-methoxy-1-octadecylcarbamoyloxypropane III a1 as colorless crystals in 85% 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 chloroform-n-hexane mixture

Quellen und Nachweise

ORD-Eintrag
ord-be78dc49d7c042619c378dea97416892
Quelldatensatz
uspto-grants-1992_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05138067

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