Hydrochloric Acid → N-(Chloroacetyl)-2-methylalanine

HRID 2415398Notes

Reaction equation

HRID 2415398 reaction equation
[NH2:1][C:2]([CH3:7])([CH3:6])[C:3]([OH:5])=[O:4].[OH-].[Na+].[Cl:10][CH2:11][C:12](Cl)=[O:13].Cl>O>[Cl:10][CH2:11][C:12]([NH:1][C:2]([CH3:7])([CH3:6])[C:3]([OH:5])=[O:4])=[O:13]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6119Aminoisobutyric acidHCID 6577Chloroacetyl chlorideHCID 14798Sodium Hydroxide2×

Product 1

HCID 17605750N-(Chloroacetyl)-2-methylalanineYield 62.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
5 °C

Procedure

To a stirring mixture of 2-aminoisobutyric acid (165.8 g; 1.61 mol), sodium hydroxide (64.4 g; 1.61 mol) and 800 ml water cooled to 5° C., was added chloroacetyl chloride (200 g; 1.77 mol) and then a solution of sodium hydroxide (70.8 g; 1.77 mol) in 143 ml water. The temperature was maintained between 5 to 10° C. during the additions. The reaction mixture was then allowed to warm to room temperature and the solution was acidified with 165 ml of concentrated aqueous HCl. The precipitated solid was filtered and dried under vacuum to afford 180.4 g (62%) of product.

Workup

  1. temperatureThe temperature was maintained between 5 to 10° C. during the additions
  2. temperatureto warm to room temperature
  3. filtrationThe precipitated solid was filtered
  4. customdried under vacuum

Sources & evidence

ORD record
ord-62b43340f40e4044be41c8f0273e65ce
Source dataset
uspto-grants-2004_11
Patent number
US06818716B2

Reaction notes

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