Bromoacetic Acid → N-succinimidyl bromoacetate

HRID 1525808Notes

Reaction equation

HRID 1525808 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 was 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 was 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-f3d77f111b214cf58cdcc08a6cd3f363
Source dataset
uspto-grants-2015_07
Patent number
US09085563B2

Reaction notes

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