Pyridine → N-acetyl-2-methylalanine

HRID 2286614Notes

Reaction equation

HRID 2286614 reaction equation
[NH2:1][C:2]([CH3:7])([CH3:6])[C:3]([OH:5])=[O:4].N1C=CC=CC=1.[C:14](OC(=O)C)(=[O:16])[CH3:15]>O>[C:14]([NH:1][C:2]([CH3:7])([CH3:6])[C:3]([OH:5])=[O:4])(=[O:16])[CH3:15]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6119Aminoisobutyric acidHCID 7918Acetic Anhydride

Product 1

HCID 233700N-acetyl-2-methylalanineYield 63,724.301%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A suspension of 41.2 g (0.4 mmol) of alpha -aminoisobutyric acid, 100 ml pyridine, and 100 ml water is stirred at 0°-5° C. and 45.0 ml (0.45 mmol) of acetic anhydride is added over a period of 30 min. Solution is observed after 1 hr and the mixture is allowed to stand at room temperature for 10 hrs. The reaction mixture is diluted with 500 ml water and evaporated in vacuo. The residue is then recrystallized from water, dried in vacuo affording 37.0 g alpha-acetamidoisobutyric acid.

Workup

  1. waitto stand at room temperature for 10 hrs
  2. customevaporated in vacuo
  3. customThe residue is then recrystallized from water
  4. customdried in vacuo

Sources & evidence

ORD record
ord-82f0f8190d544928b2208cd4789ce9e6
Source dataset
uspto-grants-1981_05
Patent number
US04267180

Reaction notes

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