Sulfuric Acid → 3-Maleimidophenyl boronic acid

HRID 1489337

Reaction equation

HRID 1489337 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([B:8]([OH:10])[OH:9])[CH:5]=[CH:6][CH:7]=1.COC(N1[C:19](=[O:20])[CH:18]=[CH:17][C:16]1=[O:21])=O.OS(O)(=O)=O>C([O-])(O)=O.[Na+].O>[C:16]1(=[O:21])[N:1]([C:2]2[CH:3]=[C:4]([B:8]([OH:10])[OH:9])[CH:5]=[CH:6][CH:7]=2)[C:19](=[O:20])[CH:18]=[CH:17]1

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 922693-Aminophenylboronic acidHCID 580610N-(Methoxycarbonyl)maleimide

Product 1

HCID 224930233-Maleimidophenyl boronic acidYield 64.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
0 °C

Procedure

(3-Aminophenyl)boronic acid (1.26 grams, 0.01 mole) is dissolved in saturated NaHCO3 (50 ml) by briefly heating the mixture on a hot plate. The solution is cooled in an ice bath to approximately 0° C., and N-methoxycarbonylmaleimide (1.55 grams, 0.01 mole) added with vigorous stirring. After 10 min. the solution is diluted with water (200 ml) and then stirred at room temperature for 30 to 40 min. The pH is adjusted to approximately 5.5 by addition of 1M H2SO4, and the precipitate collected by filtration. The precipitate is washed with 1M H2SO4 (2×50 ml), and then dried overnight in vacuo over NaOH pellets to afford 1.39 grams (64% yield) of (3-maleimidophenyl)boronic acid. The structure was confirmed by 300 MHz, 1H NMR spectrometry in d6 -DMSO.

Workup

  1. temperatureby briefly heating the mixture on a hot plate
  2. filtrationthe precipitate collected by filtration
  3. washThe precipitate is washed with 1M H2SO4 (2×50 ml)
  4. dry with materialdried overnight in vacuo over NaOH pellets

Sources & evidence

ORD record
ord-02c3331d01104366bf1a29de582e5b34
Source dataset
uspto-grants-1997_10
Patent number
US05677431

Linked notes

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