Succinic anhydride → Succinic anhydride

HRID 725726Notes

Reaction equation

HRID 725726 reaction equation
FC1C=CC=CC=1C1C=CC(C2C(C)=C([C:25]([OH:27])=[O:26])C3C(=CC=C(CCN)C=3)N=2)=CC=1.[Na].[C:32]1(=[O:38])[O:37][C:35](=[O:36])[CH2:34][CH2:33]1.C([O-])(=O)CCC([NH-])=[O:43].[Na+].[Na+]>CN(C)C=O.C(=O)(O)[O-].[Na+].C(N(CC)CC)C>[C:35]1(=[O:36])[O:37][C:32](=[O:38])[CH2:33][CH2:34]1.[C:25](=[O:26])([O-:43])[O-:27]

Participants

9

Reactant 4

HCID 7922Succinic anhydrideHCID 5360545SodiumHCID 197085652-(2'-Fluoro-1,1'-Biphenyl-4-yl)-3-Methyl-6-(2-Aminoethyl)-4-Quinolinecarboxylic Acid3×HCID 176624977Disodium;4-azanidyl-4-oxobutanoate2×

Product 2

HCID 7922Succinic anhydrideHCID 19660Carbonate Ion

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolvent2×HCID 8471TriethylamineSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

A stock solution of succinic anhydride was prepared by dissolving 24.3 mg in 1.635 ml of dimethylformamide (DMF). 2-(2'-Fluoro-1,1'-Biphenyl-4-yl)-3-Methyl-6-(2-Aminoethyl)-4-Quinolinecarboxylic Acid, Sodium Salt (10 mg) was placed in a glass vial along with 161 μl succinic anhydride stock solution and 9 μl dry triethylamine. This was stirred overnight in the dark at room temperature. A stock solution of Disuccinimdyl carbonate (DSC) was prepared by dissolving 62.4 mg of DSC into 1.59 ml of dry DMF. 174 μl of the DSC stock and 9 μl of dry triethylamine were added to the 2-(2'-Fluoro-1,1'-Biphenyl-4-yl)-3-Methyl-6-(2-Aminoethyl)-4-Quinolinecarboxylic Acid, Sodium Salt-succinamic acid solution for activation. This was stirred for one hour in the dark at room temperature. Half of the activated 2-(2'-Fluoro-1,1'-Biphenyl-4-yl)-3-Methyl-6-(2-Aminoethyl)-4-Quinolinecarboxylic Acid, Sodium Salt-succinamic acid solution was rapidly added to either BSA or KLH solutions (26 mg protein dissolved in 43.3 ml of 0.15M sodium bicarbonate, pH 8.1) and gently agitated overnight in the dark at 4° C. After coupling, the immunogens were dialyzed against three changes of PBS to remove any free hapten and excess coupling reagents as described in Chemistry of Protein Conjugation and Cross-Linking, S. Wong, CRC Press, 1991, which is hereby incorporated by reference. Haptens were also conjugated to OA using this method.

Workup

  1. stirringThis was stirred for one hour in the dark at room temperature
  2. customthe immunogens were dialyzed against three changes of PBS
  3. customto remove any free hapten and excess coupling reagents

Sources & evidence

ORD record
ord-c2ceccacd1224d7b91a9d6595803ef29
Source dataset
uspto-grants-1998_01
Patent number
US05707844

Reaction notes

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