Acetic Acid → N-(2-Cyanoethyl)-2-methylalanine

HRID 1479038Notes

Reaction equation

HRID 1479038 reaction equation
[C:1](#[N:4])[CH:2]=[CH2:3].[NH2:5][C:6]([CH3:11])([CH3:10])[C:7]([OH:9])=[O:8].[OH-].[Na+].CC(O)=O>O>[C:1]([CH2:2][CH2:3][NH:5][C:6]([CH3:11])([CH3:10])[C:7]([OH:9])=[O:8])#[N:4]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6119Aminoisobutyric acidHCID 7855AcrylonitrileHCID 14798Sodium Hydroxide

Product 1

HCID 13601735N-(2-Cyanoethyl)-2-methylalanineYield 80%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Acrylonitrile (5.13 g, 96.9 mmol) was added to a cold (0° C.) solution of 2-amino-2-methylpropanoic acid (10 g, 96.9 mmol) and sodium hydroxide (3.9 g, 96.9 mmol) in water (40 mL) and the resulting mixture was stirred at room temperature for 16 hours. AcOH (6 mL) was added and the precipitate filtered off. The solid was taken up in 95% EtOH (50 mL) and cooled down to 0° C. for 1 hour. The precipitate was filtered off, washed with EtOH (25 mL) and dried to afford the title compound (12 g, 80%) as a white solid. 1H NMR (DMSO-d6) δ 3.37 (s, 1H), 2.70 (t, J=6.3 Hz, 2H), 2.58 (t, J=7.3 Hz, 2H), 1.16 (s, 6H).

Workup

  1. filtrationthe precipitate filtered off
  2. temperaturecooled down to 0° C. for 1 hour
  3. filtrationThe precipitate was filtered off
  4. washwashed with EtOH (25 mL)
  5. customdried

Sources & evidence

ORD record
ord-33087728b67d4529af6df297f80e0165
Source dataset
uspto-grants-2016_08
Patent number
US09403835B2

Reaction notes

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