Bromoacetic Acid → Bromoacetic Acid

HRID 2280046Notes

Reaction equation

HRID 2280046 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]>CN(C=O)C>[CH2:10]1[C:11](=[O:12])[N:7]([O:4][C:3]([CH2:2][Br:1])=[O:5])[C:8](=[O:13])[CH2:9]1.[Br:1][CH2:2][C:3]([OH:5])=[O:4]

Participants

5

Reactant 2

HCID 6227Bromoacetic AcidHCID 80170N-Hydroxysuccinimide

Product 2

HCID 6227Bromoacetic AcidHCID 3565210N-succinimidyl bromoacetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The NHS (N-hydroxy succinimide) ester of bromoacetic acid was prepared as follows: 100 mmoles of (13.9 g) of bromoacetic acid were dissolved in 50 ml of anhydrous DMF, to this solution 100 mmoles (20.6 g) of N—N-Dicyclohexylcarbodiimide were added with stirring followed by 100 mmoles of N-hydroxysuccinimide (11.9 g adjusted for 100% purity), and the mixture was stirred for 6 hours at 37° C. The mixture was then placed for 2 hours at −20° C. to accelerate the precipitation of hydroxyurea, which was removed by filtration. In the filtrate the DMF was removed under reduced pressure at 45° C. and the active ester was recrystallized from 2-propanal.

Workup

  1. additionwere added
  2. stirringthe mixture was stirred for 6 hours at 37° C
  3. customthe precipitation of hydroxyurea, which
  4. customwas removed by filtration
  5. customIn the filtrate the DMF was removed under reduced pressure at 45° C.
  6. customthe active ester was recrystallized from 2-propanal

Sources & evidence

ORD record
ord-0e5106f49c404a1184af7aec482beafb
Source dataset
uspto-grants-2015_09
Patent number
US09134302B2

Reaction notes

Loading…