1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → N-(2-hydroxybutanoyl)glycine benzyl ester

HRID 1092922Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1092922
[OH:1][CH:2]([CH2:6][CH3:7])[C:3]([O-])=[O:4].[Li+].C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:20]([O:27][C:28](=[O:31])[CH2:29][NH2:30])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>C(#N)C>[CH2:20]([O:27][C:28](=[O:31])[CH2:29][NH:30][C:3](=[O:4])[CH:2]([OH:1])[CH2:6][CH3:7])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Komponenten

6

Edukt 4

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 6451311O-benzylglycine toluene-p-sulphonateHCID 23707041Lithium 2-hydroxybutanoate

Produkt 1

HCID 66589261N-(2-hydroxybutanoyl)glycine benzyl esterAusbeute 49 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

1.50 g (13.6 mmol) of lithium 2-hydroxybutanoate, 4.60 g (13.6 mmol) of glycine benzyl ester p-toluenesulfonic acid salt, and 1.84 g (1.36 mmol) of 1-hydroxybenzotriazole monohydrate (HOBt) were added to 80 mL of acetonitrile and stirred at room temperature for 20 minutes. The mixture was further mixed with 2.61 g (13.6 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC) and stirred at room temperature overnight. After the reaction mixture was filtered, the filtrate was vacuum-concentrated and the residue was dissolved in 200 mL of ethyl acetate. Washing with 1N hydrochloric acid and an aqueous solution saturated sodium hydrogen carbonate was carried out successively and drying over anhydrous sodium sulfate was carried out. After the solvent as removed by distillation, the residue was purified by flash column chromatography on silica gel (No. 9385, Merck) using a solvent mixture of hexane and ethyl acetate at 1:2 ratio to obtain N-(2-hydroxybutanoyl)glycine benzyl ester as a colorless oily substance (1.67 g, yield 49%).

Aufarbeitung

  1. stirringstirred at room temperature overnight
  2. filtrationAfter the reaction mixture was filtered
  3. concentrationthe filtrate was vacuum-concentrated
  4. dissolutionthe residue was dissolved in 200 mL of ethyl acetate
  5. washWashing with 1N hydrochloric acid
  6. dry with materialdrying over anhydrous sodium sulfate
  7. customAfter the solvent as removed by distillation
  8. customthe residue was purified by flash column chromatography on silica gel (No
  9. additiona solvent mixture of hexane and ethyl acetate at 1:2 ratio

Quellen und Nachweise

ORD-Eintrag
ord-524e7b564c4d44d38389264200a88cd8
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08129557B2

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