Water → HCID 22253670, compound

HRID 1064547Notes

Reaction equation

HRID 1064547 reaction equation
[NH2:1][C:2]([CH3:7])([CH3:6])[C:3]([OH:5])=[O:4].[OH-].[Na+].O.[Br:11][CH:12]([CH3:16])[C:13](Br)=[O:14]>C(Cl)(Cl)Cl>[Br:11][CH:12]([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 79047Propanoyl bromide, 2-bromo-

Product 1

HCID 22253670HCID 22253670, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Conditions

Temperature
-12 °C

Procedure

To a stirring mixture of 2-aminoisobutyric acid (52.08 g, 0.51 mol), sodium hydroxide (20.20 g, 0.51 mol), 200 mL water, and 50 mL chloroform cooled to −12° C., was added a solution of 2-bromopropionyl bromide (100 g, 0.46 mol) in 150 mL chloroform over 15 minutes. The temperature was maintained between −15 and −12° C. during the addition. The reaction mixture was then allowed to warm to room temperature and the precipitated solid was filtered. The solid was mixed with 700 mL hot toluene, and then cooled. The white solid was then filtered and dried under vacuum. A yield of 77.60 g (70%) was obtained.

Workup

  1. temperatureThe temperature was maintained between −15 and −12° C. during the addition
  2. temperatureto warm to room temperature
  3. filtrationthe precipitated solid was filtered
  4. additionThe solid was mixed with 700 mL hot toluene
  5. temperaturecooled
  6. filtrationThe white solid was then filtered
  7. customdried under vacuum
  8. customA yield of 77.60 g (70%) was obtained

Sources & evidence

ORD record
ord-65929cf8ae0640f0aaa83641c2cb9974
Source dataset
uspto-grants-2005_11
Patent number
US06969749B2

Reaction notes

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