N-Hydroxysuccinimide → 4-{2-[2-(2-Methoxy-ethoxy)-ethoxy]-ethoxy}-butyric acid 2,5-dioxo-pyrrolidin-1-yl ester

HRID 513880Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 513880
[OH:1][N:2]1[C:6](=[O:7])[CH2:5][CH2:4][C:3]1=[O:8].CCN=C=NCCCN(C)C.Cl.[CH3:21][O:22][CH2:23][CH2:24][O:25][CH2:26][CH2:27][O:28][CH2:29][CH2:30][O:31][CH2:32][CH2:33][CH2:34][C:35](O)=[O:36]>C(Cl)Cl>[O:8]=[C:3]1[CH2:4][CH2:5][C:6](=[O:7])[N:2]1[O:1][C:35](=[O:36])[CH2:34][CH2:33][CH2:32][O:31][CH2:30][CH2:29][O:28][CH2:27][CH2:26][O:25][CH2:24][CH2:23][O:22][CH3:21]

Komponenten

5

Edukt 3

HCID 80170N-HydroxysuccinimideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 57890900m-PEG4-(CH2)3-acid

Produkt 1

HCID 578909114-{2-[2-(2-Methoxy-ethoxy)-ethoxy]-ethoxy}-butyric acid 2,5-dioxo-pyrrolidin-1-yl esterAusbeute 43 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel3×

Versuchsvorschrift

N-hydroxysuccinimide (0.55 g, 4.8 mmol) and EDCl (1.15 g, 6.0 mmol) were dissolved in CH2Cl2 (7 mL). Then 4-{2-[2-(2-Methoxy-ethoxy)-ethoxy]-ethoxy}-butyric acid (0.940 g, 3.8 mmol), dissolved in CH2Cl2 (2 mL), was added. Reaction stirred overnight at room temperature. Crude reaction was diluted with CH2Cl2 (21 mL), washed 1M HCl (30 mL), H2O (30 mL), dried MgSO4, and evaporated to dryness. Column chromatography (Silica, ethyl acetate) afforded 4, a clear oil (0.556 g, 43% yield).

Aufarbeitung

  1. additionwas added
  2. customReaction
  3. customCrude reaction
  4. washwashed 1M HCl (30 mL), H2O (30 mL), dried MgSO4
  5. customevaporated to dryness
  6. customColumn chromatography (Silica, ethyl acetate) afforded 4

Quellen und Nachweise

ORD-Eintrag
ord-b50c2b62164b4fe39c55290b093e0596
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09102758B2

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