Dimethylamine → Benzyl N-[3-(dimethylcarbamoyl)propyl]carbamate

HRID 17424

Reaktionsgleichung

Reaktionsgleichung von HRID 17424
[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][CH2:14][C:15]([OH:17])=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[CH2:19]([N:21]=[C:22]=NCCCN(C)C)C.CN(CCCN=C=NCC)C.ON1C2C=CC=CC=2N=N1.CNC>CN(C)C=O>[CH3:19][N:21]([CH3:22])[C:15]([CH2:14][CH2:13][CH2:12][NH:11][C:9](=[O:10])[O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:17]

Komponenten

6

Edukt 4

HCID 674DimethylamineHCID 211844-(((Benzyloxy)carbonyl)amino)butanoic acidHCID 757711-HydroxybenzotriazoleHCID 866308461-(Dimethylaminopropyl)-3-ethylcarbodiimide 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride

Produkt 1

HCID 16754355Benzyl N-[3-(dimethylcarbamoyl)propyl]carbamateAusbeute 82,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

4-(Benzyloxycarbonylamino)butyric acid (0.74 g, 3.12 mmol) was dissolved in N,N-dimethylformamide, then 1-(dimethylaminopropyl)-3-ethylcarbodiimide 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.60 g, 3.13 mmol), 1-hydroxybenzotriazole (0.48 g, 3.13 mmol) and dimethylamine (2.0 M tetrahydrofuran solution, 2.40 ml, 4.80 mmol) were added, followed by stirring at room temperature for 3 days. The reaction liquid was concentrated under reduced pressure, diluted with ethyl acetate, washed with water, and dried over anhydrous sodium sulfate. The solvent was evaporated away under reduced pressure, and the resulting residue was purified by silica gel column chromatography (dichloromethane:methanol=70:1 to 40:1) to obtain a yellow solid (0.68 g, 82%).

Aufarbeitung

  1. customThe reaction liquid
  2. concentrationwas concentrated under reduced pressure
  3. additiondiluted with ethyl acetate
  4. washwashed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated away under reduced pressure
  7. customthe resulting residue was purified by silica gel column chromatography (dichloromethane:methanol=70:1 to 40:1)

Quellen und Nachweise

ORD-Eintrag
ord-3c82f86e57194445b5a85b886244c1a5
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737166B2

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