4-Methoxyphenol → Methacryloylglycylglycine

HRID 978179

Reaction equation

HRID 978179 reaction equation
[NH2:1][CH2:2][C:3]([NH:5][CH2:6][C:7]([OH:9])=[O:8])=[O:4].[C:10](Cl)(=[O:14])[C:11]([CH3:13])=[CH2:12].[OH-].[Na+].COC1C=CC(O)=CC=1>>[C:10]([NH:1][CH2:2][C:3]([NH:5][CH2:6][C:7]([OH:9])=[O:8])=[O:4])(=[O:14])[C:11]([CH3:13])=[CH2:12]

Participants

5

Reactant 4

HCID 90154-MethoxyphenolHCID 11163GlycylglycineHCID 13528Methacryloyl chlorideHCID 14798Sodium Hydroxide

Product 1

HCID 10241886Methacryloylglycylglycine

Procedure

The procedure described above is utilized with 132 g (0.1 mol) of glycylglycine, 105 g of methacryloyl chloride, 80 g of sodium hydroxide and 500 mg of p-methoxyphenol at 0°-5° C. White precipitate is formed from the reaction mixture. The precipitate crystallized from water had a melting point of (192°-196° C.). Yield of product was 150 g (70.8%). NMR (DMSO-d6), 11 gamma (s, 1H, COOH), 7.9 gamma (s, 2H, NH), 5.5 gamma (s, 1H, =CH2C), 5.2 gamma (s, 1H, =CH2), 3.5 gamma (d, 4H, CH2), 2.6 gamma (s, 3H, CH3).

Workup

  1. customWhite precipitate is formed from the reaction mixture
  2. customThe precipitate crystallized from water
  3. customa melting point of (192°-196° C.)

Sources & evidence

ORD record
ord-7512288f4ae64b6b97219e387bba9822
Source dataset
uspto-grants-1987_05
Patent number
US04663409

Linked notes

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