Hydrochloric Acid → Glutamine-methacrylamide

HRID 48449

Reaktionsgleichung

Reaktionsgleichung von HRID 48449
[C:1](=O)([O-])[O-].[K+].[K+].[NH2:7][C@H:8]([C:14]([OH:16])=[O:15])[CH2:9][CH2:10][C:11](=[O:13])[NH2:12].C(Cl)(=O)C(C)=C.Cl.[Cl-].[Na+]>O.C(#N)C>[C:11]([NH2:12])(=[O:13])[C:10]([CH3:1])=[CH2:9].[NH2:7][C@H:8]([C:14]([OH:16])=[O:15])[CH2:9][CH2:10][C:11](=[O:13])[NH2:12]

Komponenten

8

Edukt 5

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 5961L-GlutamineHCID 11430Potassium CarbonateHCID 13528Methacryloyl chloride

Produkt 1

HCID 131724368Glutamine-methacrylamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

Potassium carbonate(34.55 g) was dissolved in 100 ml of distilled water, 7.30 g of L-glutamine was dissolved in the solution, and 20 ml of acetonitrile was further added to the solution. The reaction mixture was added dropwise with 10.45 g of methacryloyl chloride over about 10 minutes with vigorous stirring, and further stirred for about 2 hours. The reaction mixture was adjusted to pH 1-2 with concentrated hydrochloric acid, saturated with sodium chloride, and extracted 2 times with 100 ml of ethyl acetate. The obtained aqueous layer was extracted 3 times with 100 ml of ethyl acetate/isopropanol=1/1. The ethyl acetate/isopropanol layers were combined, concentrated, and purified on a silica gel column (30 g of silica gel, eluted with chloroform/methanol=2/1). The corresponding fractions were collected and concentrated (colorless syrup, 7.47 g)

Aufarbeitung

  1. additionwas further added to the solution
  2. extractionextracted 2 times with 100 ml of ethyl acetate
  3. extractionThe obtained aqueous layer was extracted 3 times with 100 ml of ethyl acetate/isopropanol=1/1
  4. concentrationconcentrated
  5. custompurified on a silica gel column (30 g of silica gel, eluted with chloroform/methanol=2/1)
  6. customThe corresponding fractions were collected
  7. concentrationconcentrated (colorless syrup, 7.47 g)

Quellen und Nachweise

ORD-Eintrag
ord-cf277342e5414e43ab06aca9ef7dfcf3
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06703468B1

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