1,4,8,11-Tetraazacyclotetradecane → 4-((1,4,8,11-Tetraazacyclotetradec-1-yl)methyl)benzoic acid

HRID 507796

Reaktionsgleichung

Reaktionsgleichung von HRID 507796
[NH:1]1[CH2:14][CH2:13][CH2:12][NH:11][CH2:10][CH2:9][NH:8][CH2:7][CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Cl[CH2:16][C:17]1[CH:25]=[CH:24][C:20]([C:21]([OH:23])=[O:22])=[CH:19][CH:18]=1>C(O)C.O.[Li+].[OH-]>[N:1]1([CH2:16][C:17]2[CH:25]=[CH:24][C:20]([C:21]([OH:23])=[O:22])=[CH:19][CH:18]=2)[CH2:14][CH2:13][CH2:12][NH:11][CH2:10][CH2:9][NH:8][CH2:7][CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1

Komponenten

5

Edukt 2

HCID 649641,4,8,11-TetraazacyclotetradecaneHCID 742344-(Chloromethyl)benzoic acid

Produkt 1

HCID 1305774-((1,4,8,11-Tetraazacyclotetradec-1-yl)methyl)benzoic acidAusbeute 66,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3939Lithium HydroxideLösungsmittelHCID 19096565Water ethanolLösungsmittel

Versuchsvorschrift

To solution of Cyclam (0.913 g, 4.5 mmol) dissolved in a mixture of ethanol:water (5:1 by vol.) (18 ml) was added a solution of 4-chloromethylbenzoic acid (0.157 g, 0.92 mmol) in aqueous LiOH (53 mg in 4 ml of water). This mixture was thereafter refluxed vigorously with stirring for 5 hours. Then the solvent was removed at reduced pressure, and the residue was dissolved in 13 ml of water. The aqueous solution obtained was then extracted with chloroform (10 times 3 ml) and the aqueous layer was concentrated at reduced pressure down to 2 ml. The product as a white solid was precipitated by adding the solution of concentrated HCl and ethanol and purified by recrystallizing from ethanol/water/HCl to yield 0.205 g of the title compound. According to the LC-MS, the assay of 4-(1,4,8,11-tetraazacyclotetradec-1-ylmethyl)-benzoic acid hydrochloride was >95%.

Aufarbeitung

  1. temperatureThis mixture was thereafter refluxed vigorously
  2. customThen the solvent was removed at reduced pressure
  3. dissolutionthe residue was dissolved in 13 ml of water
  4. customThe aqueous solution obtained
  5. extractionwas then extracted with chloroform (10 times 3 ml)
  6. concentrationthe aqueous layer was concentrated at reduced pressure down to 2 ml
  7. customThe product as a white solid was precipitated
  8. additionby adding the solution of concentrated HCl and ethanol
  9. custompurified
  10. customby recrystallizing from ethanol/water/HCl

Quellen und Nachweise

ORD-Eintrag
ord-de8ef36700004b8288cb30135dc12e5f
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07786292B2

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