Bromoacetic Acid → N-succinimidyl bromoacetate

HRID 2254833Notes

Reaction equation

HRID 2254833 reaction equation
[Br:1][CH2:2][C:3]([OH:5])=[O:4].C1(N=C=NC2CCCCC2)CCCCC1.O[N:22]1[C:26](=[O:27])[CH2:25][CH2:24][C:23]1=[O:28]>C(Cl)Cl>[CH2:25]1[C:26](=[O:27])[N:22]([O:4][C:3]([CH2:2][Br:1])=[O:5])[C:23](=[O:28])[CH2:24]1

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 (20 mmoles) was treated with dicyclohexyl-carbodiimide (22 mmoles, 1.1 equivalents) and N-hydroxysuccinimide (22 mmoles) in 30 ml CH2Cl2 at 4° C. according to the procedure of M. S. Bernatowicz and G. R. Matsueda (Anal. Biochem. 155:95, 1986) to give the N-succinimidyl bromoacetate as a white solid.

Sources & evidence

ORD record
ord-316e1d8932b64619972eeab06afd543f
Source dataset
uspto-grants-1993_08
Patent number
US05237016

Reaction notes

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