Reaction #44316

ord-5f8e5d07e27c4cbb8e72a0fb83256796

Reaction equation

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

Reactants

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

Reagents

None

Solvents

Cc1ccccc1
toluene

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Temperaturethe solution heated
  2. 2
    Temperatureat reflux under Dean-Stark conditions for two days
  3. 3
    OtherThe solvent was removed
  4. 4
    Otherthe residue purified by silica column chromatography
  5. 5
    Washeluting with 25-40% ethyl acetate in hexane

Procedure

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.

Source

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