Acetate → 2-(2-Guanidinoethoxy)ethyl acetate

HRID 766

Reaktionsgleichung

Reaktionsgleichung von HRID 766
C(O)(=O)C[CH2:3][C:4]([OH:6])=[O:5].O[CH2:10][CH2:11][O:12][CH2:13][CH2:14][NH:15][C:16]([NH2:18])=[NH:17].C(OC(=O)C)(=O)C.C([O-])(=O)C>C(N(CC)CC)C>[C:4]([O:6][CH2:10][CH2:11][O:12][CH2:13][CH2:14][NH:15][C:16]([NH2:18])=[NH:17])(=[O:5])[CH3:3]

Komponenten

5

Edukt 3

HCID 175AcetateHCID 7918Acetic AnhydrideHCID 178418465HCID 178418465, Verbindung

Produkt 1

HCID 1784182412-(2-Guanidinoethoxy)ethyl acetateAusbeute 40 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

2.06 g (9.99 mmol) of 2-(2-hydroxyethoxy)ethylguanidine succinate, 8 ml of triethylamine, 0.122 mg (1.0 mmol) of 4-N,N-dimethylaminopyridine and 1.02 g (9.99 mmol) of acetic anhydride were placed in a 50 ml two neck flask and were stirred for 1 hour at room temperature. After the upper phase was removed by decantation, the obtained crude product was washed five times with 50 ml of diethylether. The product was purified by a silica gel column chromatography (eluent, chloroform/ethanol=2/1 containing 0.5% acetic acid) to obtain 1.00 g of the title compound (starch syrup-like, 4.0 mmol, 40.0% in yield) in the form of acetate. Results of the analysis of this compound are as follows.

Aufarbeitung

  1. customAfter the upper phase was removed by decantation
  2. customthe obtained crude product
  3. washwas washed five times with 50 ml of diethylether
  4. customThe product was purified by a silica gel column chromatography (eluent, chloroform/ethanol=2/1 containing 0.5% acetic acid)

Quellen und Nachweise

ORD-Eintrag
ord-84fae49193d148f395e8e28f50d554ab
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05723133

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