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2-Dimethylaminopyridine → Hexadecanoic acid (2-oxo-4-pentadec-1-enyl-[1,3]dioxan-5-yl)-amide

HRID 45978
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 45978
[C:1]([NH:18][C@H:19]([C@@H:22](/[CH:24]=[CH:25]/[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])[OH:23])[CH2:20][OH:21])(=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].C1C(=O)N(OC(ON2C(=O)CCC2=O)=O)[C:41](=[O:42])C1.CN(C1C=CC=CN=1)C>C1COCC1>[O:42]=[C:41]1[O:23][CH:22]([CH:24]=[CH:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])[CH:19]([NH:18][C:1](=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[CH2:20][O:21]1
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Komponenten

5

Edukt 3

HCID 218852-DimethylaminopyridineHCID 676246Di(succinimido) carbonateHCID 5283564C16-Ceramide

Produkt 1

HCID 66790703Hexadecanoic acid (2-oxo-4-pentadec-1-enyl-[1,3]dioxan-5-yl)-amide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

N-palmitoylsphingosine (C16-ceramide, 1.61 g, 3 mmol) was dissolved in dry THF (100 ml) with heating. The clear solution was brought to room temperature and N,N′-disuccinimidyl carbonate (1.92 g, 7.5 mmol) was added. Dimethylaminopyridine (DMAP 0.81 g, 7.5 mmol) was added with stirring and the reaction further stirred for 16 hours. The solvent was removed under reduced pressure and the residue was re-crystallized from n-heptane yielding 1.3 g (68%) of disuccinimidylceramidyl carbonate as white powder m.p. 73-76° C.

Aufarbeitung

  1. temperaturewith heating
  2. customwas brought to room temperature
  3. customthe reaction
  4. stirringfurther stirred for 16 hours
  5. customThe solvent was removed under reduced pressure
  6. customthe residue was re-crystallized from n-heptane yielding 1.3 g (68%) of disuccinimidylceramidyl carbonate as white powder m.p. 73-76° C.

Quellen und Nachweise

ORD-Eintrag
ord-abf6e0ea3c46465c801339b128107511
Quelldatensatz
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08541605B2

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