Triethylamine → HCID 21881064, Verbindung

HRID 724512Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 724512
[CH3:1][O:2][C:3]1[CH:29]=[CH:28][C:6]([CH2:7][O:8][C:9]([C:11]2([C:16]([O:18][CH2:19][C:20]3[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=3)=[O:17])[CH2:14][CH:13](O)[CH2:12]2)=[O:10])=[CH:5][CH:4]=1.[C:30]1(=[O:44])[N:34]([CH2:35][CH2:36][O:37][CH2:38][CH2:39][C:40](O)=[O:41])[C:33](=[O:43])[CH:32]=[CH:31]1.C(N(CC)CC)C.[I-].ClC1C=CC=C[N+]=1C>ClCCl>[CH3:27][O:26][C:23]1[CH:24]=[CH:25][C:20]([CH2:19][O:18][C:16]([C:11]2([C:9]([O:8][CH2:7][C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:29][CH:28]=3)=[O:10])[CH2:14][CH:13]([C:40](=[O:41])[CH2:39][CH2:38][O:37][CH2:36][CH2:35][N:34]3[C:30](=[O:44])[CH:31]=[CH:32][C:33]3=[O:43])[CH2:12]2)=[O:17])=[CH:21][CH:22]=1

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 1670692-Chloro-1-methylpyridinium iodideHCID 21881060HCID 21881060, VerbindungHCID 218810653-(2-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)ethoxy)propanoic acid

Produkt 1

HCID 21881064HCID 21881064, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A solution of PMB-CB-OH (1.97 g, 4.91 mmol), 6-maleinimido-4-oxacaproic acid (1.57 g, 7.37 mmol) and triethylamine (2.04 ml, 8.64 mmol) is admixed with 2-chloro-1-methylpyridinium iodide (1.88 g, 7.37 mmol) in 30 ml anhydrous dichloromethane and stirred for three hours at room temperature. It is diluted with 140 ml dichloromethane, washed each time twice with 80 ml in hydrochloric acid, 80 ml water and once each time with 80 ml sodium chloride solution (saturated) and dried over magnesium sulfate. Subsequently the solvent is removed in a vacuum and the residue is purified by column chromatography (silica gel, chloroform/methanol 200:1). 2.89 g PMB-CB-1-Mal (99% of theory) is obtained as a colourless oil.

Aufarbeitung

  1. washwashed each time twice with 80 ml in hydrochloric acid
  2. dry with material80 ml water and once each time with 80 ml sodium chloride solution (saturated) and dried over magnesium sulfate
  3. customSubsequently the solvent is removed in a vacuum
  4. customthe residue is purified by column chromatography (silica gel, chloroform/methanol 200:1)
  5. custom2.89 g PMB-CB-1-Mal (99% of theory) is obtained as a colourless oil

Quellen und Nachweise

ORD-Eintrag
ord-ac9c726ad13140cc95022aeb4c1c7ef0
Quelldatensatz
uspto-grants-2006_11
Patentnummer
US07141691B2

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