Water → HCID 22253669, compound

HRID 226199Notes

Reaction equation

HRID 226199 reaction equation
[NH2:1][C:2]([CH3:7])([CH3:6])[C:3]([OH:5])=[O:4].[OH-].[Na+].O.[Br:11][C:12]([CH3:17])([CH3:16])[C:13](Br)=[O:14]>C(Cl)(Cl)Cl>[Br:11][C:12]([CH3:17])([CH3:16])[C:13]([NH:1][C:2]([CH3:7])([CH3:6])[C:3]([OH:5])=[O:4])=[O:14]

Participants

6

Reactant 4

HCID 962WaterHCID 6119Aminoisobutyric acidHCID 14798Sodium HydroxideHCID 886852-Bromo-2-methylpropionyl bromide

Product 1

HCID 22253669HCID 22253669, compoundYield 33.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Conditions

Temperature
-10 °C

Procedure

A stirring mixture of 2-aminoisobutyric acid (28.5 g, 0.28 mol), sodium hydroxide (11.1 g, 0.28 mol), 115 mL of water, and 30 mL of chloroform was cooled to −10° C. and stirred vigorously while a solution of 2-bromisobutyryl bromide (57.0 g, 0.25 mol) in 85 mL of chloroform was added dropwise. When addition was complete, the reaction flask was removed from the cold bath and allowed to warm to room temperature. The mixture stirred for 15 hours. Concentrated HCl (10 mL) was then added to the mixture and stirring was continued for another 30 minutes. A white solid (32.0 g) was filtered off, and the aqueous and organic phases of the filtrate were separated. The organic phase was dried over magnesium sulfate, filtered, and evaporated at reduce pressure to leave a white solid (21.0 g). The two solid portions were combined and recrystallized from toluene to afford 27.1 g (43%) of the title compound as a white solid with IR and NMR spectra consistent with the desired product.

Workup

  1. additionwas added dropwise
  2. additionWhen addition
  3. customthe reaction flask was removed from the cold bath
  4. temperatureto warm to room temperature
  5. additionConcentrated HCl (10 mL) was then added to the mixture
  6. stirringstirring
  7. waitwas continued for another 30 minutes
  8. filtrationA white solid (32.0 g) was filtered off
  9. customthe aqueous and organic phases of the filtrate were separated
  10. dry with materialThe organic phase was dried over magnesium sulfate
  11. filtrationfiltered
  12. customevaporated

Sources & evidence

ORD record
ord-b3bd110eb8474612aa358bd19140582a
Source dataset
uspto-grants-2009_07
Patent number
US07557177B2

Reaction notes

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