Reaktion #2024

ord-c0cd0c63904c42eabebf3989bb71e6b3

Reaktionsgleichung

O=C1OC2(OC=C(c3ccccc3)C2=O)c2ccccc21
fluorescamine
O=C(ON1C(=O)CC(S(=O)(=O)[O-])C1=O)C1CCC(CN2C(=O)C=CC2=O)CC1.[Na+]
Sulfo-SMCC
Cl.Cl.NCCN
ethylenediamine dihydrochloride
→
NCCN
ethylenediamine
O=C(ON1C(=O)CC(S(=O)(=O)[O-])C1=O)C1CCC(CN2C(=O)C=CC2=O)CC1.[Na+]
sulfo-SMCC

Edukte

O=C1OC2(OC=C(c3ccccc3)C2=O)c2ccccc21
fluorescamine
O=C(ON1C(=O)CC(S(=O)(=O)[O-])C1=O)C1CCC(CN2C(=O)C=CC2=O)CC1.[Na+]
Sulfo-SMCC
Cl.Cl.NCCN
ethylenediamine dihydrochloride

Reagenzien

Keine

Lösungsmittel

CC(=O)[O-].[Na+]
sodium acetate

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeWhen reaction
  2. 2
    Wascheneluted with a gradient of acetonitrile in triethanolamine/water, pH 7

Vorschrift

Sulfo-SMCC (1 eq.)(Pierce Chemical Co., Rockford, Ill.) is dissolved in sodium acetate buffer (pH 7) and ethylenediamine dihydrochloride (5 eq.) is added. The reaction is monitored by TLC visualized with fluorescamine. When reaction is complete the reaction mixture is applied directly to a C18 reverse-phase HPLC column and eluted with a gradient of acetonitrile in triethanolamine/water, pH 7. The excess ethylene diamine elutes at the solvent front, followed by the desired product. A small amount of double coupled material formed by the condensation of one molecule of ethylenediamine with two molecules of sulfo-SMCC elutes last. The desired material is characterized by 1H NMR and IR spectroscopy, mass spectrometry, and elemental analysis.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05728369uspto-grants-1998_03