Reaction #302862

ord-e4a4856015b747faa4a7eb10e50a9f34

Reaction equation

CCCCCCCCCCCCCCCC(=O)C(O)C(O)C(O)C(=O)CCCCCCCCCCCCCCC.O=C(O)CCC(=O)O
dipalmitoylglycerol succinate
O=C(n1ccnc1)n1ccnc1
carbonyldiimidazole
NCCc1c[nH]cn1
histamine
→
CCCCCCCCCCCCCCCC(=O)C(O)C(O)C(O)C(=O)CCCCCCCCCCCCCCC.NCCc1c[nH]cn1.O=C(O)CCC(=O)O
histamine dipalmitoylglycerol succinate

Reactants

CCCCCCCCCCCCCCCC(=O)C(O)C(O)C(O)C(=O)CCCCCCCCCCCCCCC.O=C(O)CCC(=O)O
dipalmitoylglycerol succinate
O=C(n1ccnc1)n1ccnc1
carbonyldiimidazole
NCCc1c[nH]cn1
histamine

Reagents

None

Solvents

CN(C)C=O
DMF
CN(C)C=O
DMF

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    workup.STIRRINGThe mixture is stirred overnight
  2. 2
    Concentrationconcentrated thoroughly in vacuum
  3. 3
    OtherThe residue is purified

Procedure

1.7 g of dipalmitoylglycerol succinate is dissolved in 20 ml of DMF at room temperature. The solution is added with 400 mg of carbonyldiimidazole dissolved in 20 ml of DMF. The mixture is allowed to stir for 1 hour and subsequently added with 300 mg of histamine. The mixture is stirred overnight and concentrated thoroughly in vacuum. The residue is purified using column chromatography on silica gel 60, with chloroform/methanol 10:1 being used as eluant.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08192753B2uspto-grants-2012_06