Hydrochloric Acid → HCID 21130191, compound

HRID 978177Notes

Reaction equation

HRID 978177 reaction equation
[NH2:1][C@H:2]([C:7]([OH:9])=[O:8])[CH2:3][C:4]([OH:6])=[O:5].[OH-].[Na+].[C:12](Cl)(=[O:16])[C:13]([CH3:15])=[CH2:14].Cl>O.COC1C=CC(O)=CC=1>[C:12]([NH:1][C@H:2]([C:7]([OH:9])=[O:8])[CH2:3][C:4]([OH:6])=[O:5])(=[O:16])[C:13]([CH3:15])=[CH2:14]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 5960L-Aspartic AcidHCID 13528Methacryloyl chlorideHCID 14798Sodium Hydroxide2×

Product 1

HCID 21130191HCID 21130191, compoundYield 59.6%

Reagents, catalysts & solvents 2

HCID 90154-MethoxyphenolCatalystHCID 962WaterSolvent2×

Procedure

L-Aspartic acid (67 g, 0.5 mol) is dissolved in 48 g (1 mol) of sodium hydroxide in 300 ml of water and the solution is cooled down in an ice-bath. p-Methoxyphenol (50 mg) is used as an inhibitor. To the above reaction mixture, is added 58 g (0.5 mol) of methacryloyl chloride (freshly distilled) and 20 g (0.5 mol) of sodium hydroxide in 80 ml of water simultaneously at a rate to keep the reaction temperature below 5° C. The reaction is allowed to reach room temperature and stirred for another three hours. The reaction mixture is acidified to pH 3.0 with 3N HCl and extracted with ethyl acetate. The combined organic layer is washed with saturated sodium chloride solution and dried over magnesium sulfate. The dried organic layer is evaporated to dryness and crystallized from ethylacetate to yield 60 g (56%) of product. Melting point (93°-96° C.). NMR (D2O), 5.6 gamma (d, 1H, =CH2), 5.4 gamma (d, 1H, =CH 2), 2.9 gamma (d, 2H, CH2), 1.8 gamma (s, 3H, CH3).

Workup

  1. temperaturethe solution is cooled down in an ice-bath
  2. customthe reaction temperature below 5° C
  3. customto reach room temperature
  4. extractionextracted with ethyl acetate
  5. washThe combined organic layer is washed with saturated sodium chloride solution
  6. dry with materialdried over magnesium sulfate
  7. customThe dried organic layer is evaporated to dryness
  8. customcrystallized from ethylacetate

Sources & evidence

ORD record
ord-c4d9c4064be54c158a2fe770db6359ad
Source dataset
uspto-grants-1987_05
Patent number
US04663409

Reaction notes

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