Lithium Hydroxide → HCID 21844877, Verbindung

HRID 618910

Reaktionsgleichung

[NH:1]1[CH2:12][CH2:11][NH:10][CH2:9][CH2:8][NH:7][CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[CH2:13]([CH:20](Br)[C:21]([OH:23])=[O:22])[CH2:14][CH:15](Br)[C:16]([OH:18])=[O:17].[OH-].[Li+]>O>[N:1]1([CH:15]([CH2:14][CH2:13][CH:20]([N:1]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8][NH:7][CH2:6][CH2:5][NH:4][CH2:3][CH2:2]2)[C:21]([OH:23])=[O:22])[C:16]([OH:18])=[O:17])[CH2:12][CH2:11][NH:10][CH2:9][CH2:8][NH:7][CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1

Komponenten

Reaktionsbedingungen

Temperatur: 60 °C

Versuchsvorschrift

A mixture of cyclen (60.75 g, 350 mmol), meso-2,5-dibromoadipic acid (10.57 g, 35 mmol), and 1M lithium hydroxide (70 mL, 70 mmol) in water (104 mL) was heated to 60° C. under nitrogen for 170 hours. After cooling to ambient temperature, the reaction mixture was applied to an AG1X8 anion exchange column [400 mL (OH-form)]. The column was washed thoroughly with water (4 L), and the product was eluted with 0.5M acetic acid (2 L). Fractions containing product were combined, chased with water (3×200 mL) and ethanol (3×100 mL) to yield the title product (8.75 g, 51.8%) as a white, hygroscopic foam. Unreacted cyclen was reclaimed by concentration of the first 2 L of eluent and recrystallization from water. 1H NMR: (D2O) δ 2.75-2.90 (br mult, 34H), 1.52 (br, 4H). 13C NMR: (D2O) 24.3, 40.5, 41.1, 41.3, 41.6, 43.1, 44.9, 63.0, 177.1. MS (FAB): m/e 487.4 (MH+).

Aufarbeitung

temperatureAfter cooling to ambient temperature
washThe column was washed thoroughly with water (4 L)
washthe product was eluted with 0.5M acetic acid (2 L)
additionFractions containing product

Quellen und Nachweise

ORD-Eintrag: ord-a07b91f93c0e440ca4be97a435d3f3a0
Quelldatensatz: uspto-grants-1999_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05958373

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