Succinic Acid → Bisbenzimide

HRID 635146Notes

Reaction equation

HRID 635146 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]3[N:14]=[C:15]([C:17]4[CH:22]=[CH:21][C:20]5[NH:23][C:24]([NH:32][C:19]=5[CH:18]=4)=[C:25]4[CH:31]=[CH:30][C:28](=[O:29])[CH:27]=[CH:26]4)[NH:16][C:10]=3[CH:9]=2)[CH2:4][CH2:3]1.[C:33](O)(=O)[CH2:34]CC(O)=O>C(Cl)(Cl)Cl>[CH3:33][CH2:34][O:29][C:28]1[CH:30]=[CH:31][C:25]([C:24]2[NH:32][C:19]3[CH:18]=[C:17]([C:15]4[NH:16][C:10]5[CH:9]=[C:8]([N:5]6[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]6)[CH:13]=[CH:12][C:11]=5[N:14]=4)[CH:22]=[CH:21][C:20]=3[N:23]=2)=[CH:26][CH:27]=1

Participants

4

Reactant 2

HCID 1110Succinic AcidHCID 178480630HCID 178480630, compound

Product 1

HCID 1464BisbenzimideYield 80%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

In this step, synthesis of an active ester of a binding enhancer is described, which can then be easily conjugated to both the photoreactive ligand and the linker. A solution of bisbenzimidazole (6 g, 0.01 mol) dicyclohexylcarbodiimide (0.05 mol) and succinic acid (0.01 mol) in 100 mL of chloroform is stirred overnight (18-24 hrs). During this time, a white precipitate is formed. The precipitate is filtered of and washed with chloroform (2×50 mL). The combined chloroform is concentrated under vacuum in a rotary evaporator and the residue purified by flash column chromatography. The fractions containing the product is combined and concentrated under vacuum in a rotary evaporate to afford bisbenzimide succinnate ester (80%) as a white solid.

Workup

  1. customDuring this time, a white precipitate is formed
  2. filtrationThe precipitate is filtered of and
  3. washwashed with chloroform (2×50 mL)
  4. concentrationThe combined chloroform is concentrated under vacuum in a rotary evaporator
  5. customthe residue purified by flash column chromatography
  6. additionThe fractions containing the product
  7. concentrationconcentrated under vacuum in
  8. customa rotary evaporate

Sources & evidence

ORD record
ord-4df608961839458f9a7b034025118eef
Source dataset
uspto-grants-2001_02
Patent number
US06187566B1

Reaction notes

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