Reaktion #44316

ord-5f8e5d07e27c4cbb8e72a0fb83256796

Reaktionsgleichung

CC(C)(C)OC(=O)NCCCCN
N-BOC-1,4-diaminobutane
O=C1C=CC(=O)O1
maleic anhydride
→
CC(C)(C)OC(=O)NCCCCN1C(=O)C=CC1=O
title compound
CC(C)(C)OC(=O)NCCCCN1C(=O)C=CC1=O
(4-Maleimidyl-butyl)-carbamic acid tert-butyl ester

Edukte

CC(C)(C)OC(=O)NCCCCN
N-BOC-1,4-diaminobutane
O=C1C=CC(=O)O1
maleic anhydride

Reagenzien

Keine

Lösungsmittel

Cc1ccccc1
toluene

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Temperaturthe solution heated
  2. 2
    Temperaturat reflux under Dean-Stark conditions for two days
  3. 3
    SonstigeThe solvent was removed
  4. 4
    Sonstigethe residue purified by silica column chromatography
  5. 5
    Wascheneluting with 25-40% ethyl acetate in hexane

Vorschrift

To a solution of N-BOC-1,4-diaminobutane (8.324 g, 0.044 mol) in dry toluene (50 ml) was added maleic anhydride (4.336 g, 0.044 mol) and the solution heated at reflux under Dean-Stark conditions for two days. The solvent was removed and the residue purified by silica column chromatography eluting with 25-40% ethyl acetate in hexane to give the title compound, 1.461 g, 12%, as a white solid.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07736635B2uspto-grants-2010_06