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

HRID 353500Notes

Reaction equation

HRID 353500 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
50 °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 50° 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-b05c1a6d35d24886bb257369775dbb9c
Source dataset
uspto-grants-2004_06
Patent number
US06753391B1

Reaction notes

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