Bromoacetic Acid → N-succinimidyl bromoacetate

HRID 475024Notes

Reaction equation

HRID 475024 reaction equation
[Br:1][CH2:2][C:3]([OH:5])=[O:4].O[N:7]1[C:11](=[O:12])[CH2:10][CH2:9][C:8]1=[O:13].C1CCC(N=C=NC2CCCCC2)CC1>C(Cl)Cl>[Br:1][CH2:2][C:3]([O:5][N:7]1[C:11](=[O:12])[CH2:10][CH2:9][C:8]1=[O:13])=[O:4]

Participants

5

Reactant 3

HCID 6227Bromoacetic AcidHCID 10868DicyclohexylcarbodiimideHCID 80170N-Hydroxysuccinimide

Product 1

HCID 3565210N-succinimidyl bromoacetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Bromoacetic acid (4.30 g) and N-hydroxysuccinimide (4.03 g) were dissolved in DCM (25 ml). The mixture was stirred on a magnetic stirrer at room temperature. DCC was added (7.42 g) in one portion and the mixture was reacted overnight. The reaction mixture was filtered to remove dicyclohexylurea. The filter cake washed several times with DCM. The combined filtrates were washed three times with saturated aqueous sodium chloride solution (30 mL/each wash), dried over anhydrous magnesium sulfate, and filtered. The title compound was obtained as a white solid (5 g) after rotary evaporation in vacuo.

Workup

  1. customthe mixture was reacted overnight
  2. filtrationThe reaction mixture was filtered
  3. customto remove dicyclohexylurea
  4. washThe filter cake washed several times with DCM
  5. washThe combined filtrates were washed three times with saturated aqueous sodium chloride solution (30 mL/
  6. washeach wash),
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered

Sources & evidence

ORD record
ord-46c3dae3d9614c58b39f45377048bd4f
Source dataset
uspto-grants-2014_01
Patent number
US08637545B2

Reaction notes

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