Diethyl Ether → N-methacryloylasparagineamide

HRID 2261502

Reaktionsgleichung

Reaktionsgleichung von HRID 2261502
[C:1](Cl)(=[O:5])[C:2]([CH3:4])=[CH2:3].Cl.[NH2:8][C@H:9]([C:14]([NH2:16])=[O:15])[CH2:10][C:11](=[O:13])[NH2:12].C(OCC)C.C(=O)([O-])[O-].[K+].[K+]>CO.O>[C:1]([NH:16][C:14](=[O:15])[C@H:9]([CH2:10][C:11](=[O:13])[NH2:12])[NH2:8])(=[O:5])[C:2]([CH3:4])=[CH2:3]

Komponenten

7

Edukt 4

HCID 3283Diethyl Ether2×HCID 11430Potassium CarbonateHCID 13528Methacryloyl chlorideHCID 16218940(S)-2-Aminosuccinamide hydrochloride

Produkt 1

HCID 86614806N-methacryloylasparagineamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

A 11.3 ml portion of methacrylic acid chloride, 1 g of asparagineamide hydrochloride (mfd. by Kokusan Kagaku) and 50 ml of diethyl ether were put into a 300 ml capacity eggplant type flask and stirred on an ice bath. Next, 20 ml of saturated potassium carbonate aqueous solution was added dropwise thereto. Thereafter, this was stirred on an ice bath for 30 minutes and then at room temperature for 12 hours. Diethyl ether layer in the thus obtained reaction liquid was discarded, and the water layer was dissolved in 100 ml of methanol. After filtration, the filtrate was concentrated under a reduced pressure and fractionated by a silica gel column using methanol as the developing solvent. The thus obtained amide compound fraction was purified using an ion exchange resin (“Dynaion (trade name) PA 412” mfd. by Mitsubishi Kagaku) After concentration under a reduced pressure and subsequent drying under a reduced pressure, 0.43 g of colorless crystals were obtained.

Aufarbeitung

  1. stirringThereafter, this was stirred on an ice bath for 30 minutes
  2. filtrationAfter filtration
  3. concentrationthe filtrate was concentrated under a reduced pressure
  4. customThe thus obtained amide compound fraction was purified
  5. concentrationAfter concentration under a reduced pressure
  6. customsubsequent drying under a reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-2b77fb6cdb414d78b7f09e69d2abd348
Quelldatensatz
uspto-grants-2010_12
Patentnummer
US07847047B2

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