Hexadecanedioic acid → N-(15-carboxypentadecanoyloxy)phthalimide

HRID 36392

Reaktionsgleichung

Reaktionsgleichung von HRID 36392
[C:1]([OH:20])(=[O:19])[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][C:16]([OH:18])=[O:17].O[N:22]1[C:26](=[O:27])[C:25]2=[CH:28][CH:29]=[CH:30][CH:31]=[C:24]2[C:23]1=[O:32].C1CCC(N=C=NC2CCCCC2)CC1>O1CCCC1.CN(C1C=CN=CC=1)C.Cl>[C:16]([CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][C:1]([O:20][N:22]1[C:23](=[O:32])[C:24]2=[CH:31][CH:30]=[CH:29][CH:28]=[C:25]2[C:26]1=[O:27])=[O:19])([OH:18])=[O:17]

Komponenten

6

Edukt 3

HCID 10459Hexadecanedioic acidHCID 10665N-HydroxyphthalimideHCID 10868Dicyclohexylcarbodiimide

Produkt 1

HCID 21832397N-(15-carboxypentadecanoyloxy)phthalimideAusbeute 41,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11789490N,N-dimethylpyridin-4-amine HydrochlorideKatalysatorHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

In 15 ml of anhydrous tetrahydrufuran 1,16-hexadecanedioic acid (500 mg, 1.75 mmoles) was dissolved. To the obtained solution, were added a solution of N-hydroxyphthalimide (285 mg, 1.75 mmoles) in 10 ml of anhydrous tetrahydrofuran and N,N-dimethylaminopyridine hydrochloride (1.4 mg) and the mixture was stirred for 30 minutes. To the mixture was added a solution of DCC (361 mg, 1.75 mmoles) in 3 ml of anhydrous tetrahydrofuran and the resulting mixture was stirred overnight. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was separated and purified by silica gel chromatography, to give N-(15-carboxypentadecanoyloxy)phthalimide (310 mg, 41%) having the following properties.

Aufarbeitung

  1. stirringthe resulting mixture was stirred overnight
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was separated
  5. custompurified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-fa265d4281a24f07943ea5c5d3feef24
Quelldatensatz
uspto-grants-1995_05
Patentnummer
US05414089

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