Gamma-Aminobutyric Acid → 4-[(2-Methylacryloyl)amino]butanoic acid

HRID 978175Notes

Reaction equation

HRID 978175 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][C:5]([OH:7])=[O:6].[C:8](Cl)(=[O:12])[C:9]([CH3:11])=[CH2:10].[OH-].[Na+].COC1C=CC(O)=CC=1>>[C:8]([NH:1][CH2:2][CH2:3][CH2:4][C:5]([OH:7])=[O:6])(=[O:12])[C:9]([CH3:11])=[CH2:10]

Participants

5

Reactant 4

HCID 119Gamma-Aminobutyric AcidHCID 90154-MethoxyphenolHCID 13528Methacryloyl chlorideHCID 14798Sodium Hydroxide

Product 1

HCID 187981514-[(2-Methylacryloyl)amino]butanoic acid

Procedure

The general procedure above is utilized with 51.5 g (0.5 mol) of 4-aminobutyric acid, 52.39 (0.5 mol) of methacryloyl chloride, 40 g (1 mol) of sodium hydroxide. p-methoxyphenol is used as an inihibitor. Crystallization from ethyl acetate yielded very low melting crystalline material, melting point (30°-35° C.). Purity by bromination 100.14%. NMR (CDCl3), 10.85 gamma (br s, 1H, COOH), 7.1 gamma (br s, 1H, NH), 6.0 gamma (br s, 1H, =CH2), 5.65 gamma (br s, 1H, =CH2), 3.6 gamma (q, 2H, NCH2), 2.6 gamma (t, 2H, CH2CO), 2.2 gamma (br s, 5H, CH3 and CH2CH2CH2).

Workup

  1. customCrystallization from ethyl acetate
  2. customyielded very low
  3. custompoint (30°-35° C.)

Sources & evidence

ORD record
ord-64042d84db2f460c987e98529706f2bc
Source dataset
uspto-grants-1987_05
Patent number
US04663409

Reaction notes

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