Sodium Iodide → 6-((2,5-Dioxopyrrolidin-1-yl)oxy)-6-oxohexanoic acid

HRID 6334Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 6334
[C:1]([O:17]C)(=[O:16])[CH2:2][CH2:3][CH2:4][CH2:5][C:6]([O:8][N:9]1[C:13](=[O:14])[CH2:12][CH2:11][C:10]1=[O:15])=[O:7].Cl[Si](C)(C)C.[I-].[Na+]>C(#N)C.C(OCC)(=O)C>[C:10]1(=[O:15])[N:9]([O:8][C:6](=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2][C:1]([OH:17])=[O:16])[C:13](=[O:14])[CH2:12][CH2:11]1

Komponenten

6

Edukt 3

HCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 4458286Methyl N-Succinimidyl Adipate

Produkt 1

HCID 120522896-((2,5-Dioxopyrrolidin-1-yl)oxy)-6-oxohexanoic acidAusbeute 75,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of methyl succinimidyl adipate (4.5 g, 17.5 mmol), chlorotrimethylsilane (11.1 ml, 87.5 mmol) and sodium iodide (13.1 g, 87.5 mmol) in 10 ml of acetonitrile was heated at reflux for 12 hours. The mixture was then cooled to room temperature and diluted with ethyl acetate. The reaction mixture was washed repeatedly with 5 percent aqueous sodium bisulfite until the organic solution was colorless. Then it was washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated to provide 3.2 g (71 percent yield by weight) of adipic acid monosuccinimidyl ester as a white solid.

Aufarbeitung

  1. temperatureat reflux for 12 hours
  2. washThe reaction mixture was washed repeatedly with 5 percent aqueous sodium bisulfite until the organic solution
  3. washThen it was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-6ee06cc338d74b2ebea19761b8727ee9
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05248611

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