Triethylamine → m-PEG4-succinimidyl carbonate

HRID 1820586Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1820586
[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13]O.C1C(=O)N([O:22][C:23]([O:25][N:26]2[C:31](=[O:32])[CH2:30][CH2:29][C:27]2=[O:28])=[O:24])C(=O)C1.C(N(CC)CC)C.C(OCC)(=O)C.CO>C(#N)C>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][O:22][C:23](=[O:24])[O:25][N:26]1[C:27](=[O:28])[CH2:29][CH2:30][C:31]1=[O:32]

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 90263Tetraethylene glycol monomethyl etherHCID 676246Di(succinimido) carbonateHCID 21584119Ethylacetate methanol

Produkt 1

HCID 59659904m-PEG4-succinimidyl carbonateAusbeute 28 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

Tetraethylene glycol monomethyl ether (1.0 g, 4.8 mmol) and N,N′-disuccinimidyl carbonate (1.48 g, 5.8 mmol) were dissolved in acetonitrile (10 mL). Then triethylamine (1.0 mL, 7.2 mmol) was added and the reaction stirred overnight at room temperature. Crude reaction was evaporated to dryness, dissolved in sat. NaHCO3 (30 mL), washed ethyl acetate (2×30 mL), dried MgSO4, and evaporated to dryness. Column chromatography (Silica, ethyl acetate/MeOH, 20:1) afforded 1 a clear oil (0.462 g, 28% yield).

Aufarbeitung

  1. customCrude reaction
  2. customwas evaporated to dryness
  3. dissolutiondissolved in sat. NaHCO3 (30 mL)
  4. washwashed ethyl acetate (2×30 mL), dried MgSO4
  5. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-c35931f798644c229bf5c262a3c4e97c
Quelldatensatz
uspto-grants-2009_10
Patentnummer
US07605123B2

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