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

HRID 226197Notes

Reaction equation

HRID 226197 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-methylalanine

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 two separate solutions of chloroacetyl chloride (200 g, 1.77 mol) and sodium hydroxide (70.8 g, 1.77 mol) in 143 mL water. The temperature was maintained between 5 to 10° C. during the addition. The reaction mixture was then allowed to warm to room temperature and the solution was acidified with 165 mL of concentrated aq. HCl. The precipitated solid was filtered and dried under vacuum. A yield of 180.4 g (62%) was obtained.

Workup

  1. additionwas added two
  2. temperatureThe temperature was maintained between 5 to 10° C. during the addition
  3. temperatureto warm to room temperature
  4. filtrationThe precipitated solid was filtered
  5. customdried under vacuum
  6. customA yield of 180.4 g (62%) was obtained

Sources & evidence

ORD record
ord-8987d0fd68454e07baf2884aa9ba9d43
Source dataset
uspto-grants-2009_07
Patent number
US07557177B2

Reaction notes

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