Dimethylformamide → (S)-Benzyl (2-oxotetrahydrofuran-3-yl)carbamate

HRID 1439966

Reaktionsgleichung

Reaktionsgleichung von HRID 1439966
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:16]([OH:18])=[O:17])[CH2:13][CH2:14]O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ON1C2C=CC=CC=2N=N1.CN(C)C=O.Cl.C(N=C=NCCCN(C)C)C>O>[CH2:1]([O:8][C:9]([NH:11][C@H:12]1[CH2:13][CH2:14][O:18][C:16]1=[O:17])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 757711-HydroxybenzotriazoleHCID 489187Cbz-L-HomoserineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Produkt 1

HCID 489185(S)-Benzyl (2-oxotetrahydrofuran-3-yl)carbamateAusbeute 84,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of N-benzyloxycarbonyl-(L)-homoserine (9.0 g), 1-hydroxybenzotriazole (HOBt) (5.4 g) and N,N-dimethylformamide (DMF) (50 ml) was provided and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (WSCD.HCl) (7.5 g) was added to the mixture under ice-cooling. The whole mixture was stirred at room temperature for 14 hours. The reaction mixture was then poured into water and extracted with ethyl acetate. The ethyl acetate layer was washed with 1% aqueous citric acid, water, saturated aqueous sodium hydrogen carbonate and saturated aqueous sodium chloride in the order mentioned and dried over MgSO4 and the solvent was distilled off, whereby (S)-3-(N-benzyloxycarbonylamino)tetrahydrofuran-2-one (7.0 g, 84.3%) was obtained. This product was recrystallized from dichloromethane-isopropyl ether. Colorless needles, m.p. 129°-130° C. Optical rotation [α]D -0.5° (C=0.52, CHCl3).

Aufarbeitung

  1. temperaturecooling
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with 1% aqueous citric acid, water, saturated aqueous sodium hydrogen carbonate and saturated aqueous sodium chloride in the order
  4. dry with materialdried over MgSO4
  5. distillationthe solvent was distilled off

Quellen und Nachweise

ORD-Eintrag
ord-5eeee8c67d45497a852fd5dd5cfbdfa2
Quelldatensatz
uspto-grants-1996_03
Patentnummer
US05496834

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