Hydrochloric Acid → Lysine-methacrylamide

HRID 48450

Reaction equation

HRID 48450 reaction equation
C(=O)([O-])O.[K+].Cl.[NH2:7][C@H:8]([C:14]([OH:16])=[O:15])[CH2:9][CH2:10][CH2:11][CH2:12][NH2:13].[C:17](Cl)(=[O:21])[C:18]([CH3:20])=[CH2:19].Cl.[Cl-].[Na+]>O.CC(C)=O>[C:17]([NH2:7])(=[O:21])[C:18]([CH3:20])=[CH2:19].[NH2:7][C@H:8]([C:14]([OH:16])=[O:15])[CH2:9][CH2:10][CH2:11][CH2:12][NH2:13]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 13528Methacryloyl chlorideHCID 69568L-Lysine monohydrochlorideHCID 516893Potassium Bicarbonate

Product 1

HCID 88031551Lysine-methacrylamide

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

Potassium hydrogencarbonate(5.51 g) was dissolved in 100 ml of distilled water, 9.13 g of lysine hydrochloride was dissolved in the solution, and 80 ml of acetone was further added to the solution. The reaction mixture was added dropwise with 5.23 g of methacryloyl chloride over about 10 minutes with vigorous stirring under ice cooling, and further vigorously stirred for about 2 hours. The reaction mixture was adjusted to pH 1-2 with concentrated hydrochloric acid, and saturated with sodium chloride. The aqueous layer was washed twice with 100 ml of ethyl acetate, and extracted 3 times with 100 ml of ethyl acetate/isopropanol=1/2. The ethyl acetate/isopropanol layers were combined, concentrated to about 50 ml under reduced pressure, added with 500 ml of isopropanol, and again concentrated to about 200 ml. The deposited sodium chloride was removed by filtration, and the filtrate was concentrated (colorless syrup, 5.53 g)

Workup

  1. additionwas further added to the solution
  2. stirringfurther vigorously stirred for about 2 hours
  3. washThe aqueous layer was washed twice with 100 ml of ethyl acetate
  4. extractionextracted 3 times with 100 ml of ethyl acetate/isopropanol=1/2
  5. concentrationconcentrated to about 50 ml under reduced pressure
  6. additionadded with 500 ml of isopropanol
  7. concentrationagain concentrated to about 200 ml
  8. customThe deposited sodium chloride was removed by filtration
  9. concentrationthe filtrate was concentrated (colorless syrup, 5.53 g)

Sources & evidence

ORD record
ord-744101f63a93452bb2a11a400eabb871
Source dataset
uspto-grants-2004_03
Patent number
US06703468B1

Linked notes

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