Water → HCID 22253670, compound

HRID 353502Notes

Reaction equation

HRID 353502 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, compoundYield 70.4%

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; 0.463 mol) in 150 mL chloroform. The temperature was maintained between −15 to −12° C. during the addition. The reaction mixture was then allowed to warm to room temperature and stirred for 17 hours. The precipitated solid was filtered, mixed with 700 mL hot toluene, then cooled to room temperature. The solid was filtered and dried under vacuum to afford 77.6 g (70%) of product.

Workup

  1. temperatureThe temperature was maintained between −15 to −12° C. during the addition
  2. temperatureto warm to room temperature
  3. filtrationThe precipitated solid was filtered
  4. additionmixed with 700 mL hot toluene
  5. temperaturecooled to room temperature
  6. filtrationThe solid was filtered
  7. customdried under vacuum

Sources & evidence

ORD record
ord-02bde18eb2e44b0f8d2b031ef868b455
Source dataset
uspto-grants-2004_06
Patent number
US06753391B1

Reaction notes

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