Glyceric acid → HCID 20074079, Verbindung

HRID 704412

Reaktionsgleichung

Reaktionsgleichung von HRID 704412
C1(N=C=NC2CCCCC2)CCCCC1.[CH2:16]([O:23][C:24]1[CH:31]=[CH:30][C:27]([CH2:28][NH2:29])=[CH:26][CH:25]=1)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].[C:32](O)(=[O:37])[CH:33]([CH2:35][OH:36])[OH:34].ON1C2C=CC=CC=2N=N1>CN(C)C=O.C(OCC)(=O)C>[CH2:16]([O:23][C:24]1[CH:25]=[CH:26][C:27]([CH2:28][NH:29][C:35](=[O:36])[CH:33]([CH2:32][OH:37])[OH:34])=[CH:30][CH:31]=1)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

Komponenten

7

Edukt 4

HCID 752Glyceric acidHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 151155341-[4-(Heptyloxy)phenyl]methanamine

Produkt 1

HCID 20074079HCID 20074079, VerbindungAusbeute 28,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Dicyclohexylcarbodiimide (160 mg) was added to a solution of 200 mg of p-heptyloxybenzylamine, 150 mg of glyceric acid (65% aqueous solution) and 110 mg of 1-hydroxybenzotriazole in 2 ml of N,N-dimethylformamide. The reaction mixture was stirred at room temperature for 16 hours, then diluted with ethyl acetate, washed in sequence with saturated aqueous solution of sodium hydrogen carbonate, water and saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by preparative silica gel thin layer chromatography to give 80 mg of N-(p-heptyloxybenzyl)glyceramide.

Aufarbeitung

  1. washwashed in sequence with saturated aqueous solution of sodium hydrogen carbonate, water and saturated aqueous solution of sodium chloride
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by preparative silica gel thin layer chromatography

Quellen und Nachweise

ORD-Eintrag
ord-26f1cdaaf02c4cd1b785cc204e3972b6
Quelldatensatz
uspto-grants-1991_01
Patentnummer
US04987132

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